Downtown Winter Garden Events

Winter Garden Farmers Market

Saturday, June 1

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Farmers Market 16th Birthday Party on the Lawn

Saturday, June 1

9:00 am - 12:00 pm

Join us to mark the Winter Garden Farmers Market 16th Birthday with Kids’ Activities with DJ Renee, Face Painting, Collaborative Art Birthday Card, Icy Treats, & Live Music. Activities: 9:00 am-12:00 pm/Market: 8:00 am-1:00 pm. FREE

Lawn adjacent to Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “Top Choice Fine Arts 10th Annual Awards Show”

Saturday, June 1

10:00 am - 4:00 pm

SOBO’s Annual Awards Exhibition showcases the best 2D & 3D works of art. Awards are presented for Best of Show, People’s Choice, Curator’s Choice, and Multiple Medium Category Winners.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

West Orange Women: Making History, Part 2

Saturday, June 1

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, June 1

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Monday, June 3

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Tuesday, June 4

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Tuesday, June 4

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, June 4

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, June 4

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Wednesday, June 5

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Wednesday, June 5

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, June 5

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, June 5

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Thursday, June 6

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Thursday, June 6

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, June 6

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Thursday, June 6

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Fun in the Sun” ~ Opening Reception

Thursday, June 6

5:30 pm - 8:00 pm

Public Invited

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Friday, June 7

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Friday, June 7

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, June 7

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, June 7

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, June 7

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, June 8

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Fun in the Sun”

Saturday, June 8

10:00 am - 4:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

West Orange Women: Making History, Part 2

Saturday, June 8

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, June 8

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Monday, June 10

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Tuesday, June 11

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Tuesday, June 11

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, June 11

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, June 11

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Wednesday, June 12

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Wednesday, June 12

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, June 12

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, June 12

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Thursday, June 13

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Thursday, June 13

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, June 13

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Thursday, June 13

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Friday, June 14

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Friday, June 14

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, June 14

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, June 14

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, June 14

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, June 15

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Juneteenth Community Celebration

Saturday, June 15

10:00 am - 1:00 pm

Presented by City of Winter Garden and community partners, event includes family activities, guest speakers, children’s performances, kids’ zone, & more! Bring a lawn chair/blanket. Free

City Park, 1203 E. Plant Street

Art Exhibition: “Fun in the Sun”

Saturday, June 15

10:00 am - 4:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – Saturday History Series Presentation

Saturday, June 15

11:00 am - 3:00 pm

These special presentations feature the history of local railroads, the communities they served, plus topics of regional interest. Some events may require paid admission. Visit cfrhs.org/events for upcoming presentations.

Central Florida Railroad Museum, 101 S. Boyd Street

West Orange Women: Making History, Part 2

Saturday, June 15

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, June 15

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Monday, June 17

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Tuesday, June 18

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Tuesday, June 18

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, June 18

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, June 18

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Wednesday, June 19

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Wednesday, June 19

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, June 19

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, June 19

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Thursday, June 20

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Thursday, June 20

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, June 20

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Thursday, June 20

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Friday, June 21

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Friday, June 21

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, June 21

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, June 21

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, June 21

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, June 22

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Fun in the Sun”

Saturday, June 22

10:00 am - 4:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

West Orange Women: Making History, Part 2

Saturday, June 22

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, June 22

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Monday, June 24

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Tuesday, June 25

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Tuesday, June 25

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, June 25

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, June 25

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Wednesday, June 26

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Wednesday, June 26

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, June 26

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, June 26

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Thursday, June 27

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Thursday, June 27

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, June 27

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Thursday, June 27

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Selling Sunshine – The Art of Citrus Advertising”

Friday, June 28

7:30 am - 5:30 pm

This exhibit from the Winter Garden Heritage Foundation features many of the ingenious ads, spanning over a century, that were guaranteed to convince the world to purchase Florida’s liquid sunshine.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

West Orange Women: Making History, Part 2

Friday, June 28

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, June 28

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, June 28

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, June 28

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy!

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, June 29

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Fun in the Sun”

Saturday, June 29

10:00 am - 4:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

West Orange Women: Making History, Part 2

Saturday, June 29

11:00 am - 3:00 pm

The Winter Garden Heritage Foundation continues to honor the many women whose work, volunteerism, and love of community helped make West Orange County the very special place we call home. The exhibit will highlight two dozen women from the past and the present whose legacy shines today. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, June 29

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Monday, July 1

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Summertime in Winter Garden”

Tuesday, July 2

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, July 2

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, July 2

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, July 2

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Wednesday, July 3

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, July 3

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, July 3

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, July 3

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

20th All American Kids Parade 2024 – July 4

Thursday, July 4

8:00 am - 10:30 am

Start your Independence Day at this 20-year old community tradition hosted by the Winter Garden Masonic Lodge! Pancake Breakfast (kids eat free), 8-10 am. Decorate your bike, scooter, wagon, or walking shoes with red, white, and blue and join the parade (kickoff 10 am) through historic downtown. Or secure a good viewing spot along West Plant St. Free

Winter Garden Masonic Lodge, 230 W. Bay Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, July 4

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, July 4

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Party in the Park & Fireworks Display

Thursday, July 4

6:00 pm

One of the best fireworks displays in West Orange County plus live music, family activities, food vendors, and more! Festivities begin at 6:00 pm. Fireworks show at 9:15 pm. Bring a chair or blanket. Presented by the City of Winter Garden. Parking is available at Health Central Park and Dillard Street Elementary. Free.

Newton Park, 29 W. Garden Avenue

Art Exhibition: “Summertime in Winter Garden”

Friday, July 5

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, July 5

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, July 5

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, July 5

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, July 5

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, July 6

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Fun in the Sun”

Saturday, July 6

10:00 am - 4:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, July 6

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, July 6

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Monday, July 8

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Summertime in Winter Garden”

Tuesday, July 9

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, July 9

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, July 9

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, July 9

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Wednesday, July 10

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, July 10

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, July 10

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, July 10

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Thursday, July 11

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, July 11

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, July 11

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Thursday, July 11

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Friday, July 12

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, July 12

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, July 12

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, July 12

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, July 12

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, July 13

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Fun in the Sun”

Saturday, July 13

10:00 am - 4:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – Archive Day at the Museum

Saturday, July 13

11:00 am - 3:00 pm

Browse the museum’s archives of railroad memorabilia including documents, photos, timetables, menus, maps, and ephemera. An Archivist will be available to answer questions, and the library will also be open to visitors. Free Admission

Central Florida Railroad Museum, 101 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, July 13

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, July 13

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Monday, July 15

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Summertime in Winter Garden”

Tuesday, July 16

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, July 16

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, July 16

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, July 16

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Wednesday, July 17

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, July 17

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, July 17

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, July 17

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Thursday, July 18

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, July 18

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, July 18

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Thursday, July 18

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Friday, July 19

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, July 19

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, July 19

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, July 19

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, July 19

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, July 20

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Fun in the Sun”

Saturday, July 20

10:00 am - 4:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, July 20

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, July 20

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Monday, July 22

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Summertime in Winter Garden”

Tuesday, July 23

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, July 23

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, July 23

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, July 23

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Wednesday, July 24

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, July 24

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, July 24

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, July 24

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Thursday, July 25

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, July 25

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, July 25

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Thursday, July 25

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Sip ‘n Shop Event — Sip into Summer with Downtown Merchants

Thursday, July 25

4:00 pm - 8:00 pm

Cool off with some late night local shopping! Enjoy a mixture of special offers, summer sips & nibbles, local vendor pop-ups & more at participating stores. Grab a friend or two and come out and support your small local downtown merchants this summer season.

Historic Downtown Winter Garden

Art Exhibition: “Summertime in Winter Garden”

Friday, July 26

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Where’s Waldo Scavenger Hunt in Downtown Winter Garden

Friday, July 26

10:00 am - 8:00 pm

Come join Writer's Block Bookstore for a search party for Waldo. Waldo is hiding in our store and others throughout downtown, and it is your mission to follow the scavenger hunt to find Waldo! Activities and crafts will be provided for attendees all day long…come join in on the fun! FREE. Registration is not required, but recommended (one ticket per family). Click image for details & to sign up.

Writer's Block Bookstore, 32 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, July 26

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, July 26

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, July 26

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, July 26

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, July 27

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Fun in the Sun”

Saturday, July 27

10:00 am - 4:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, July 27

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, July 27

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Monday, July 29

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Summertime in Winter Garden”

Tuesday, July 30

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, July 30

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Tuesday, July 30

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Tuesday, July 30

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Summertime in Winter Garden”

Wednesday, July 31

7:30 am - 5:30 pm

Local artists respond to the City of Winter Garden’s call to illustrate what summertime is like in Winter Garden. Stop inside City Hall for some summertime sunshine to see this exhibit of various mediums of art created by community artists.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, July 31

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Wednesday, July 31

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Wednesday, July 31

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Thursday, August 1

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, August 1

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Thursday, August 1

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Thursday, August 1

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Friday, August 2

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, August 2

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Friday, August 2

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Friday, August 2

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, August 2

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, August 3

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Downtown Summer Sidewalk Sale & LIVE MUSIC

Saturday, August 3

9:00 am - 10:00 pm

This annual Summer Sidewalk Sale is a great time to snag boutique apparel, accessories, home décor, and more at discounted prices. PLUS, LIVE OUTDOOR MUSIC & fun for KIDS with FREE GELATO on Main St. (11am-4pm) and FREE BACK-TO-SCHOOL KIDS CRAFT at SOBO Art Gallery (10am-2pm). Hours & participation varies by merchant.

Historic Downtown Winter Garden

One Last Roar: A History of the Winter Garden Lions Club

Saturday, August 3

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Fun in the Sun”

Saturday, August 3

11:00 am - 5:00 pm

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Dining in Style: The Golden Age of the Railroad Dining Car

Saturday, August 3

11:00 am - 3:00 pm

This special temporary exhibit recalls the days when a scrumptious meal on a train was enjoyed in a Stylish setting as small towns and scenic vistas passed your window. Free

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Monday, August 5

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Tuesday, August 6

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, August 6

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Tuesday, August 6

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Wednesday, August 7

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, August 7

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Wednesday, August 7

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Thursday, August 8

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, August 8

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Thursday, August 8

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “Form & Figure” ~ Opening Reception

Thursday, August 8

5:30 pm - 8:00 pm

Join us for the Opening Reception of SOBO Art Gallery's exhibition, "Form & Figure.," Free.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Friday, August 9

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, August 9

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Friday, August 9

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Fridays on the Plaza

Friday, August 9

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

National Farmers Market Week Celebration at Winter Garden Farmers Market

Saturday, August 10

8:00 am - 1:00 pm

Pay tribute to your backyard farmers market in honor of National Farmers Market Week. Enjoy FREE KIDS CRAFT ACTIVITY (at Parking Garage Plaza),100+ vendors, local farm booths, and live music! Kids Craft Activity: 9am-12pm/Market: 8am-1pm

Downtown Pavilion, 104 S. Lakeview Avenue

Winter Garden Farmers Market

Saturday, August 10

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Form & Figure”

Saturday, August 10

10:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, August 10

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Monday, August 12

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Tuesday, August 13

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, August 13

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Tuesday, August 13

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Wednesday, August 14

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, August 14

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Wednesday, August 14

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Thursday, August 15

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, August 15

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Thursday, August 15

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Friday, August 16

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, August 16

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Friday, August 16

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Fridays on the Plaza

Friday, August 16

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, August 17

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Form & Figure”

Saturday, August 17

10:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, August 17

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Monday, August 19

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Tuesday, August 20

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, August 20

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Tuesday, August 20

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Wednesday, August 21

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, August 21

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Wednesday, August 21

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Thursday, August 22

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, August 22

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Thursday, August 22

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Friday, August 23

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, August 23

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Friday, August 23

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Fridays on the Plaza

Friday, August 23

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, August 24

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Form & Figure”

Saturday, August 24

10:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, August 24

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Monday, August 26

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Tuesday, August 27

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, August 27

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Tuesday, August 27

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Wednesday, August 28

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, August 28

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Wednesday, August 28

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Thursday, August 29

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, August 29

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Thursday, August 29

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “School Bells Are Ringing – Winter Garden’s Lakeview and Charles R. Drew High Schools”

Friday, August 30

7:30 am - 5:30 pm

Presented by the Winter Garden Heritage Foundation, this exhibit shows that education has been a priority in the region since the very beginning.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, August 30

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, August 30

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Friday, August 30

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Fridays on the Plaza

Friday, August 30

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, August 31

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Form & Figure”

Saturday, August 31

10:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, August 31

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, August 31

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, September 3

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, September 3

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, September 3

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, September 3

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Tuesday, September 3

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Wednesday, September 4

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, September 4

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, September 4

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, September 4

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Wednesday, September 4

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Thursday, September 5

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, September 5

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, September 5

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, September 5

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Thursday, September 5

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Friday, September 6

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, September 6

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, September 6

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, September 6

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Friday, September 6

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Fridays on the Plaza

Friday, September 6

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, September 7

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Form & Figure”

Saturday, September 7

10:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, September 7

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, September 7

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, September 7

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Tony DeSare Concert presented by Central Florida Jazz Society

Sunday, September 8

3:00 pm - 5:00 pm

Join us for an unforgettable afternoon with the incredibly talented Tony DeSare. Don’t miss your chance to see this world-renowned artist perform live. Click image to get your tickets now before they sell out!

Pilars, 146 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Monday, September 9

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, September 10

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, September 10

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, September 10

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, September 10

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Tuesday, September 10

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Wednesday, September 11

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, September 11

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, September 11

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, September 11

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Wednesday, September 11

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Thursday, September 12

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, September 12

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, September 12

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, September 12

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Thursday, September 12

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Friday, September 13

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, September 13

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Form & Figure”

Friday, September 13

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Fridays on the Plaza

Friday, September 13

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, September 14

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Form & Figure”

Saturday, September 14

10:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, September 14

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Monday, September 16

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, September 17

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, September 17

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Form & Figure”

Tuesday, September 17

11:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Wednesday, September 18

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, September 18

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, September 18

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, September 18

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Wednesday, September 18

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Thursday, September 19

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, September 19

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, September 19

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, September 19

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Thursday, September 19

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Winter Garden Heritage Museum: Heroes from Florida in World War II

Thursday, September 19

6:00 pm - 8:00 pm

Join us for a presentation about Florida’s World War II heroes. Light refreshments provided. Free admission. Click image to register.

Winter Garden Heritage Foundation Heller Hall, 21 E. Plant Street

Art Exhibition: “¡Viva El Arte!”

Friday, September 20

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, September 20

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, September 20

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, September 20

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Friday, September 20

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Fridays on the Plaza

Friday, September 20

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, September 21

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

SOBO Art Gallery: Pinwheels for Peace ~ Create a Free Pinwheel & Plant It!

Saturday, September 21

9:00 am - 12:00 pm

All ages welcome to design a pinwheel and include a message of peace on its stake and plant it on the SOBO Art Gallery lawn for display in celebration of International Peace Day. All materials provided complimentary. Please allow 40 minutes to complete. All children must be accompanied by an adult. Click image to reserve a pinwheel. Free.

SOBO Art Gallery, 127 S. Boyd Street

Art Exhibition: “Form & Figure”

Saturday, September 21

10:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, September 21

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, September 21

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, September 21

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Central Florida Railroad Museum – Saturday History Series Presentation

Saturday, September 21

1:30 pm - 2:30 pm

Florida: A history of pictures - Railroads Edition presented by Mike McGinness and Jeff Davies.

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Monday, September 23

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, September 24

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, September 24

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, September 24

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Tuesday, September 24

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Tuesday, September 24

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Wednesday, September 25

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, September 25

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, September 25

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Wednesday, September 25

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Wednesday, September 25

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Thursday, September 26

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, September 26

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, September 26

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Thursday, September 26

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Thursday, September 26

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Harvest Sip ‘n Shop Event — Fall into Season with Late Night Shopping (CANCELED)

Thursday, September 26

5:00 pm - 8:00 pm

Fall into season with some late night sips, fun, and shopping. Grab a friend or two and come out and support your small local downtown merchants this fall season.

Historic Downtown Winter Garden

Art Exhibition: “¡Viva El Arte!”

Friday, September 27

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, September 27

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, September 27

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Friday, September 27

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Form & Figure”

Friday, September 27

11:00 am - 5:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum: Stories from Disney’s Animation Renaissance by Author Michael Lyons

Friday, September 27

7:00 pm - 9:00 pm

Take a trip back into time to a fantastic era of Disney animation with author Michael Lyons' story of the studio's comeback with their hit animated films in the 1990s. Tickets: $15/per person. Click image to purchase.

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, September 27

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, September 28

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Art Exhibition: “Form & Figure”

Saturday, September 28

10:00 am - 4:00 pm

Explore ideas related to the importance of Form and Figure in Artistic Expression in all mediums of 2D & 3D works. Free Admission.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, September 28

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, September 28

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

One Last Roar: A History of the Winter Garden Lions Club

Saturday, September 28

11:00 am - 3:00 pm

The Winter Garden chapter of the Lions Club disbanded in April 2023 but left an indelible legacy of service to the region. This exhibit will document and showcase the history of this group of people whose dedication to the gift of sight led to fundraising efforts that helped thousands of people. Artifacts, medals, banners, photographs, and much more will grace the Winter Garden Heritage Museum to honor this vital organization. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Monday, September 30

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, October 1

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, October 1

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, October 1

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

National Night Out – Free Community Event

Tuesday, October 1

6:00 pm - 9:00 pm

Hosted by the Winter Garden Police Department, this free annual event includes children’s activities, food, music, raffles, meet and greet with your local police officers, crime prevention tips, and lots of fun! FREE

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “¡Viva El Arte!”

Wednesday, October 2

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, October 2

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, October 2

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Thursday, October 3

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, October 3

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, October 3

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

SOBO Art Gallery & Studio Exhibitions: Harvest Palette

Thursday, October 3

5:30 pm - 8:00 pm

Join us for the Opening Reception of SOBO Art Gallery's exhibition, "Harvest Palette", Free.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “¡Viva El Arte!”

Friday, October 4

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, October 4

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, October 4

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Fridays on the Plaza

Friday, October 4

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

LiveTrends Boutique Birthday Party

Saturday, October 5

8:00 am - 2:00 pm

LiveTrends Boutique is celebrating the third year anniversary of its downtown retail store with a Birthday Party including LIVE MUSIC, Plant Giveaways, Arts & Crafts, Scavenger Hunt, and more! Don't miss the fun!

LiveTrends Boutique, 279 Tremaine Street

Winter Garden Farmers Market

Saturday, October 5

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, October 5

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, October 5

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Monday, October 7

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, October 8

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, October 8

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, October 8

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Wednesday, October 9

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, October 9

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, October 9

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Thursday, October 10

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, October 10

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, October 10

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Friday, October 11

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, October 11

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, October 11

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Fridays on the Plaza

Friday, October 11

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, October 12

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, October 12

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, October 12

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Central Florida Jazz Society: UCF Flying Horse Big Band Concert

Sunday, October 13

3:00 pm - 5:00 pm

The chart-topping UCF Flying Horse Big Band will be swingin’ and groovin’ at this month's Central Florida Jazz Society concert. The band is composed of students in UCF’s jazz studies program. The Flying Horse Big Band performs at festivals and concert halls regionally and nationally. Click image for tickets.

Pilars Loft, 146 W Plant Street

Art Exhibition: “¡Viva El Arte!”

Monday, October 14

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, October 15

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, October 15

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, October 15

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Wednesday, October 16

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, October 16

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, October 16

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “¡Viva El Arte!”

Thursday, October 17

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, October 17

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, October 17

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Halloween Experience WITH NIGHTTIME ENTERTAIMENT

Friday, October 18

All Day/Entertainment at Night. City hosts a 14-day family-friendly spooky Halloween Experience throughout Downtown with special live entertainment tonight: Halloween Light Show on City Hall (7-9pm), Street Performers (6-9pm), Hay Maze at City Hall (4-9pm) Halloween- and Fall-Themed Photo Spots, Outdoor Seasonal Decorations & Light Displays, and more!

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Friday, October 18

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Halloween Spooktacular Preschool Program

Friday, October 18

10:00 am - 12:00 pm

Preschoolers ages 3 - 5, come in your Halloween costume to enjoy fall carnival games, holiday-themed crafts, and trick or treating! Hosted by the Parks & Recreation Department, friends and preschool classes are welcome too! Preschools, please call 407.656.4155 in advance for registration.

Jessie Brock Community Center, 310 North Dillard Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, October 18

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, October 18

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Heritage Museum: Speaker Series with Jim Crescitelli

Friday, October 18

6:30 pm - 8:00 pm

To celebrate the Winter Garden Heritage Foundation's 30th year, Director Jim Crescitelli will devote an evening to covering the history of our beloved city. The program features a PowerPoint presentation and rare local artifacts. Refreshments will be on hand. Free!

Winter Garden Heritage Foundation Heller Hall, 21 E. Plant Street

Fridays on the Plaza

Friday, October 18

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Ghost & Ghouls Harvest Sale

Saturday, October 19

All day event (hours vary by merchant). Join us in celebrating Halloween with Downtown Winter Gardens Ghost & Ghouls Harvest Sale. Enjoy spooky decorations and even spookier sales! Hosted by participating downtown shops.

Historic Downtown Winter Garden

Winter Garden Halloween Experience WITH NIGHTTIME ENTERTAIMENT

Saturday, October 19

All Day/Entertainment at Night. City hosts a 14-day family-friendly spooky Halloween Experience throughout Downtown with special live entertainment tonight: Halloween Light Show on City Hall (7-9pm), Street Performers (6-9pm), Hay Maze at City Hall (8am-9pm) Halloween- and Fall-Themed Photo Spots, Outdoor Seasonal Decorations & Light Displays, and more!

Historic Downtown, 300 W. Plant Street

Winter Garden Farmers Market

Saturday, October 19

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, October 19

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, October 19

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Central Florida Railroad Museum – Archives Day at the Museum

Saturday, October 19

11:00 am - 3:00 pm

Our Archives has thousands of documents, photos, timetables, menus, maps and more. Once a quarter, we'll showcase some of these items in our meeting room and answer your questions about the railroads and trains they represented. Free admission.

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Halloween Experience WITH NIGHTTIME ENTERTAIMENT

Sunday, October 20

All Day/Entertainment at Night. City hosts a 14-day family-friendly spooky Halloween Experience throughout Downtown with special live entertainment tonight: Halloween Light Show on City Hall (7-9pm), Street Performers (6-9pm), Hay Maze at City Hall (9am-9pm) Halloween- and Fall-Themed Photo Spots, Outdoor Seasonal Decorations & Light Displays, and more!

Historic Downtown, 300 W. Plant Street

Create a Haunted House ~ Family Event at SOBO Art Gallery

Sunday, October 20

3:00 pm - 4:30 pm

Work together to turn a prepared cereal box on a base into an awesome “Haunted House.” All materials and step-by-step guidance are provided. $38 per house for 1 adult with 1 child. Click image to register.

SOBO Art Gallery, 127 S. Boyd Street

Winter Garden Halloween Experience

Monday, October 21

All Day. City hosts a 14-day Halloween Experience for the community! Downtown turns family-friendly spooky with a Hay Maze (10am-9pm) outside City Hall, outdoor Seasonal Decorations & Light Displays throughout, Halloween- and Fall-themed Photo Spots, and more! FREE

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Monday, October 21

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Winter Garden Halloween Experience

Tuesday, October 22

All Day. City hosts a 14-day Halloween Experience for the community! Downtown turns family-friendly spooky with a Hay Maze (10am-9pm) outside City Hall, outdoor Seasonal Decorations & Light Displays throughout, Halloween- and Fall-themed Photo Spots, and more! FREE

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, October 22

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, October 22

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, October 22

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Halloween Experience

Wednesday, October 23

All Day. City hosts a 14-day Halloween Experience for the community! Downtown turns family-friendly spooky with a Hay Maze (10am-9pm) outside City Hall, outdoor Seasonal Decorations & Light Displays throughout, Halloween- and Fall-themed Photo Spots, and more! FREE

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Wednesday, October 23

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, October 23

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, October 23

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Halloween Experience

Thursday, October 24

All Day. City hosts a 14-day Halloween Experience for the community! Downtown turns family-friendly spooky with a Hay Maze (10am-9pm) outside City Hall, outdoor Seasonal Decorations & Light Displays throughout, Halloween- and Fall-themed Photo Spots, and more! FREE

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Thursday, October 24

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, October 24

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, October 24

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Halloween Experience WITH NIGHTTIME ENTERTAIMENT

Friday, October 25

All Day/Entertainment at Night. City hosts a 14-day family-friendly spooky Halloween Experience throughout Downtown with special live entertainment tonight: Halloween Light Show on City Hall (7-9pm), Street Performers (6-9pm), Hay Maze at City Hall (10am-9pm) Halloween- and Fall-Themed Photo Spots, Outdoor Seasonal Decorations & Light Displays, and more!

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Friday, October 25

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, October 25

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, October 25

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Frightfully Fun Lego Night at the Railroad Museum

Friday, October 25

5:00 pm - 8:00 pm

A ticketed event to see a Halloween and holiday-themed custom-built Lego Train layout plus fun activities including Lego block fun table, photo booth, coloring table, music, History Hunt map, Treats, and spooky decorations. Under 18 must have an adult with the group. Proceeds benefit the museum. Click image to purchase tickets.

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, October 25

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Halloween Experience WITH NIGHTTIME ENTERTAIMENT

Saturday, October 26

All Day/Entertainment at Night. City hosts a 14-day family-friendly spooky Halloween Experience throughout Downtown with special live entertainment tonight: Halloween Light Show on City Hall (7-9pm), Street Performers (6-9pm), Hay Maze at City Hall (8am-9pm) Halloween- and Fall-Themed Photo Spots, Outdoor Seasonal Decorations & Light Displays, and more!

Historic Downtown, 300 W. Plant Street

Halloween at the Farmers Market

Saturday, October 26

8:00 am - 1:00 pm

Free Halloween craft making at the kids’ tent (Parking Garage Plaza, 9 am – 12 pm), live music, fall-themed photo spot and a great place to find pumpkins of all sizes for carving.

Downtown Pavilion, 104 S. Lakeview Avenue

Lego Day at the Railroad Museum

Saturday, October 26

9:00 am - 4:00 pm

It's a frightfully fun day for visitors to see the visiting large Lego train layout loaded with buildings, people, trains, and a replica of the Orlando Train Station - with a Halloween and holiday twist. Courtesy of the Greater Florida Lego Users Group, the event will take place during Downtown's Halloween Experience and museum so be sure to stop in. Click image for details.

Central Florida Railroad Museum, 101 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, October 26

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, October 26

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Halloween Experience WITH NIGHTTIME ENTERTAIMENT

Sunday, October 27

All Day/Entertainment at Night. City hosts a 14-day family-friendly spooky Halloween Experience throughout Downtown with special live entertainment tonight: Halloween Light Show on City Hall (7-9pm), Street Performers (6-9pm), Hay Maze at City Hall (9am-9pm) Halloween- and Fall-Themed Photo Spots, Outdoor Seasonal Decorations & Light Displays, and more!

Historic Downtown, 300 W. Plant Street

Winter Garden Halloween Experience

Monday, October 28

All Day. City hosts a 14-day Halloween Experience for the community! Downtown turns family-friendly spooky with a Hay Maze (10am-9pm) outside City Hall, outdoor Seasonal Decorations & Light Displays throughout, Halloween- and Fall-themed Photo Spots, and more! FREE

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Monday, October 28

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Winter Garden Halloween Experience

Tuesday, October 29

All Day. City hosts a 14-day Halloween Experience for the community! Downtown turns family-friendly spooky with a Hay Maze (10am-9pm) outside City Hall, outdoor Seasonal Decorations & Light Displays throughout, Halloween- and Fall-themed Photo Spots, and more! FREE

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Tuesday, October 29

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, October 29

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, October 29

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Halloween Experience

Wednesday, October 30

All Day. City hosts a 14-day Halloween Experience for the community! Downtown turns family-friendly spooky with a Hay Maze (10am-9pm) outside City Hall, outdoor Seasonal Decorations & Light Displays throughout, Halloween- and Fall-themed Photo Spots, and more! FREE

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Wednesday, October 30

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, October 30

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, October 30

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Halloween Experience WITH NIGHTTIME ENTERTAIMENT

Thursday, October 31

All Day/Entertainment at Night. City hosts a 14-day family-friendly spooky Halloween Experience throughout Downtown with special live entertainment tonight: Halloween Light Show on City Hall (7-9pm), Street Performers (6-9pm), Hay Maze at City Hall (10am-9pm) Halloween- and Fall-Themed Photo Spots, Outdoor Seasonal Decorations & Light Displays, and more!

Historic Downtown, 300 W. Plant Street

Art Exhibition: “¡Viva El Arte!”

Thursday, October 31

7:30 am - 5:30 pm

Curated by the Winter Garden Art Association, this exhibit features various forms of 2-D and 3-D artistic expressions from Central Florida Hispanic Artists. These colorful works of art are sure to brighten your day! Free.

Art in Public Places Gallery in City Hall, 300 W Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, October 31

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, October 31

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Downtown Merchants host Trick-or-Treat

Thursday, October 31

3:00 pm - 5:00 pm

Nearly 20 downtown merchants will host a Trick-or-Treat event to provide free candy to youth trick-or-treaters.

Historic Downtown Winter Garden

Spooky Caboose at the History Center

Thursday, October 31

3:00 pm - 8:00 pm

Climb the steps into the dark recesses of Plant Street's beloved Caboose for family-friendly frights, free treats - and maybe some tricks. Fun for all ages! Free to enter, donations appreciated.

Winter Garden History, Education, and Visitors’ Center, 21 E. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, November 1

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, November 1

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, November 1

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Fridays on the Plaza

Friday, November 1

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

American Legion 8th Annual Challenge 22 Ruck Walk

Saturday, November 2

7:00 am - 3:00 pm

Come out to the Challenge 22 2.2-mile tribute walk and activities Ruck Walk to support the efforts to prevent PTS Suicide of Veterans. Click image to register for the walk and/or to donate.

American Legion Post #63, Historic Downtown, 271 W. Plant Street

Health & Harvest Festival at the Winter Garden Farmers Market

Saturday, November 2

8:00 am - 1:00 pm

Hosted by Heathy West Orange & City of Winter Garden at the Winter Garden Farmers Market, event includes children & fitness activities, games, giveaways, cooking & gardening fun, health screenings, and more! FREE

Downtown Pavilion, 104 S. Lakeview Ave

Donut Dash 5K Run/Walk

Saturday, November 2

8:00 am - 11:00 am

Run or walk through the timeless neighborhoods as you start/finish at Lake Apopka! We will have music, kids fun run, t-shirts, medals, Krispy Kreme Donuts, and best donut costume prize. Presented by WGPAL.

Newton Park, 1 Surprise Drive

Winter Garden Farmers Market

Saturday, November 2

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, November 2

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, November 2

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 4

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, November 5

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, November 5

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, November 5

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 6

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, November 6

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, November 6

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, November 7

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, November 7

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, November 7

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Downtown Merchants Host Jingle ‘n’ Mingle

Thursday, November 7

5:00 pm - 8:00 pm

Kick off the holiday celebrations with some late night shopping fun, at select locations, in downtown Winter Garden.

Historic Downtown Winter Garden

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, November 8

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, November 8

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, November 8

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Central Florida Railroad Museum: Books and Movies in Motion

Friday, November 8

6:00 pm - 8:00 pm

Train Documentary Producer & Author Richard Luckin will talk about the railroad books written and films produced during their careers prior to a screening of Selling Sunshine: The Florida Trains.

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, November 8

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, November 9

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

City of Winter Garden Annual Craft Affair

Saturday, November 9

10:00 am - 2:00 pm

Arts & crafts lovers of all ages are invited to shop for unique and one-of-a-kind items handmade by our 50+ creative friends. Perfect timing for holiday shopping! Free to attend.

Jessie Brock Community Center, 310 N. Dillard Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, November 9

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, November 9

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Heritage Museum: Movie Premiere of The Train Station in American Life

Saturday, November 9

6:00 pm - 8:00 pm

Join us for the Movie Premiere of The Train Station in American Life. The film’s producer Richard Luckin and writer Bonnie Hansen will be on hand to introduce the film and host a Q&A following the movie.

Winter Garden Heritage Foundation Heller Hall, 21 E. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 11

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, November 12

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, November 12

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, November 12

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 13

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, November 13

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, November 13

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, November 14

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, November 14

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, November 14

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, November 15

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, November 15

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, November 15

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

A Florida Citrus Hall of Fame Program: When Tiaras Ruled…A History of the Miss Florida Citrus Pageant

Friday, November 15

6:30 pm - 8:30 pm

Come meet the reigning Miss Florida! Executive Director of the Florida Citrus Hall of Fame, Brenda Eubanks Burnette, will share the fascinating history of the organization's Miss Florida Citrus and Citrus Queen honorees. Take a nostalgic journey as we celebrate the legacy and heritage of the Florida Citrus Queen and Miss Florida Citrus through the years. Free!

Winter Garden Heritage Foundation Heller Hall, 21 E. Plant Street

Fridays on the Plaza

Friday, November 15

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Winter Garden Farmers Market

Saturday, November 16

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, November 16

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, November 16

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 18

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, November 19

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, November 19

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, November 19

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 20

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, November 20

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, November 20

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, November 21

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, November 21

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, November 21

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Winter Garden Heritage Museum: Speaker Series with Rick Cronin

Thursday, November 21

6:30 pm - 8:00 pm

Join author and Central Florida historian, Rick Cronin for his presentation of: The Chase Brothers & Company - The Making of the Sunniland Dynasty. Discover how this iconic family's legacy began in 1884 in Sanford and grew to shape the state's citrus production. Free!

Winter Garden Heritage Foundation Heller Hall, 21 E. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, November 22

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, November 22

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, November 22

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Fridays on the Plaza

Friday, November 22

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Thanksgiving at the Farmers Market

Saturday, November 23

8:00 am - 1:00 pm

Free Thanksgiving craft making at the kids’ tent (Parking Garage Plaza, 9 am – 12 pm), live music, and a great place for fresh produce, desserts, décor, and more for your Thanksgiving celebration.

Downtown Pavilion, 104 S. Lakeview Avenue

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, November 23

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, November 23

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 25

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, November 26

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, November 26

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, November 26

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 27

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, November 27

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, November 27

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, November 29

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Fridays on the Plaza

Friday, November 29

7:00 pm - 9:00 pm

City of Winter Garden presents outdoor live musical entertainment every Friday night in the center of historic downtown. Enjoy while you stroll, dine, and shop, or grab a nearby swing to enjoy! Click image for entertainment line-up.

Downtown Winter Garden, Centennial Plaza Gazebo

Small Business Saturday

Saturday, November 30

Historic Downtown Winter Garden hosts an ALL DAY holiday shopping kick-off event with LIVE MUSIC (11 am - 8 pm) to celebrate Small Business Saturday. LOVE LOCAL while enjoying the festive fun and holiday wonderland. Shop small to have a big impact! All Day

Historic Downtown

Winter Garden Farmers Market

Saturday, November 30

8:00 am - 1:00 pm

Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, November 30

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, November 30

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, December 2

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, December 3

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, December 3

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, December 3

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Christmas Trivia Night at Crooked Can Brewing Company

Tuesday, December 3

7:30 pm

Crooked Can's monthly themed night in December is Christmas Trivia. The event will feature four rounds of 5 questions each, a halftime question, and a Jeopardy-style final question. Join us for an entertaining night of fun and trivia!

426 W Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, December 4

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, December 4

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, December 4

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, December 5

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, December 5

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, December 5

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

SOBO Art Gallery Studio Exhibition & OPENING RECEPTION : Reflections of Joy

Thursday, December 5

5:30 pm - 8:00 pm

Join us for the Opening Reception of SOBO Art Gallery's exhibition, "Reflections of Joy", Free.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, December 6

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Reflections of Joy”

Friday, December 6

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, December 6

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, December 6

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Light Up Winter Garden

Friday, December 6

6:00 pm - 9:00 pm

Welcome the holiday season with the Light Up Winter Garden event. Tree/street lighting, live holiday entertainment, children’s activities, and more! Sponsored by Duke Energy & City of Winter Garden. Ceremony: 6:00 pm, Street Lighting: 6:15 pm. Free.

West Plant Street, Historic Downtown

Christmas in the Garden Big Band Extravaganza

Friday, December 6

6:30 pm

Led by Dove Award winning artist, Clay Crosse, and an all-star band, the big show will immediately follow Light Up Winter Garden on the front steps of First Baptist Church Winter Garden. Join us for this exciting outdoor Christmas concert with surprise special guests, including the Foundation Academy Steel Drum Band. Free to attend.

Winter Garden's First Baptist Church, 125 E. Plant Street

A Very Merry Farmers Market

Saturday, December 7

8:00 am - 1:00 pm

The festive-decorated market is ideal for shopping for gifts, seasonal décor, as well as for fresh produce and artisan foods for your holiday celebrations.

Downtown Pavilion, 104 S. Lakeview Avenue

Winter Garden Christmas Parade

Saturday, December 7

10:00 am

This long-standing Winter Garden holiday tradition will delight spectators and bring in holiday cheer! Look for the Big Guy himself at the end of the parade! Free.

Kick off from S. Dillard Street and E. Plant Street

Art Exhibition: “Reflections of Joy”

Saturday, December 7

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, December 7

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, December 7

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

The Winter Garden Polar Express

Saturday, December 7

12:00 pm - 2:00 pm

All aboard! Enjoy a reading of The Polar Express and take in the magical journey on the Winter Garden Heritage Foundation Train while visiting local shops along the way. Click image for more information!

Downtown Winter Garden

Holiday Night Market at Downtown

Saturday, December 7

4:00 pm - 8:00 pm

Roam Freely through the holiday wonderland of downtown as booths of festive treats, décor, and gift ideas line the pedestrian-only streets. Holiday-themed live entertainment and activities add to the festivities. Fun for all ages, gather friends and family for this merry experience.

Historic Downtown

Winter Garden Christmas Golf Cart Parade

Saturday, December 7

6:00 pm

Prepare to be amazed by the holiday-themed decorated golf carts as they parade through historic downtown.

West Plant Street, Historic Downtown

A Merry Winter Garden Light Show

Saturday, December 7

6:00 pm - 9:00 pm

Spectacular animated holiday-themed light show synchronized to music projected onto the front façade of Winter Garden City Hall. Free.

Winter Garden City Hall, 300 W. Plant Street

Steve Luciano Jazz Concert Presented by the Central Florida Jazz Society

Sunday, December 8

3:00 pm - 5:00 pm

Get ready to be captivated by the incredible talent of jazz guitarist Steve Luciano! Tickets can be purchased at the door or by clicking the image.

Pilars, 146 W Plant Street

Create a Gingerbread House ~ Family Event at SOBO Art Gallery

Sunday, December 8

3:00 pm - 4:30 pm

Create a Gingerbread House together – a perfect decoration for the holiday! All materials and step-by-step guidance are provided. $52 per house for 1 adult with 1 child. $6 each for additional artists working on the same house. Click image to register.

SOBO Art Gallery, 127 S. Boyd Street

A Merry Winter Garden Light Show

Sunday, December 8

6:00 pm - 9:00 pm

Spectacular animated holiday-themed light show synchronized to music projected onto the front façade of Winter Garden City Hall. Free.

Winter Garden City Hall, 300 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, December 9

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Horse Drawn Holiday Carriage Tours

Monday, December 9

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, December 10

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Reflections of Joy”

Tuesday, December 10

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, December 10

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, December 10

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Holiday Flix at the Garden

Tuesday, December 10

4:00 pm

It's a Wonderful Life movie screening presented by Holiday Flix at the Garden. Enjoy this festive flix in the timeless ambiance of the Garden Theatre while visiting the Holiday Wonderland in historic downtown Winter Garden. Ticket:$5. Click image to purchase!

Garden Theatre, 160 W. Plant Street

Horse Drawn Holiday Carriage Tours

Tuesday, December 10

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, December 11

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Reflections of Joy”

Wednesday, December 11

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, December 11

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, December 11

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Horse Drawn Holiday Carriage Tours

Wednesday, December 11

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Holiday Flix at the Garden

Wednesday, December 11

7:00 pm

It's a Wonderful Life movie screening presented by Holiday Flix at the Garden. Enjoy this festive flix in the timeless ambiance of the Garden Theatre while visiting the Holiday Wonderland in historic downtown Winter Garden. Ticket:$5. Click image to purchase!

Garden Theatre, 160 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, December 12

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Reflections of Joy”

Thursday, December 12

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, December 12

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, December 12

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Downtown Merchants Host Ladies Night ~ Spirits and Sparkles

Thursday, December 12

5:00 pm - 8:00 pm

Late night shopping, refreshments and holiday fun, at select locations in downtown Winter Garden.

Historic Downtown Winter Garden

Horse Drawn Holiday Carriage Tours

Thursday, December 12

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, December 13

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Meet The Ornament King

Friday, December 13

11:00 am - 2:00 pm

Come meet The Ornament King, creator of iconic holiday designs at LiveTrends Boutique! The renowned ornament artist Christoper Radko* will talk about his creative process in this special meet and greet opportunity. *No affiliation with the Christopher Radko brand® owned by Rauch Industries Inc.

LiveTrends Boutique, 279 Tremaine St.

Art Exhibition: “Reflections of Joy”

Friday, December 13

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, December 13

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, December 13

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Sending Santa a Peppermint Mocha Latte

Friday, December 13

4:00 pm - 6:00 pm

Come meet Santa at Foxtail Coffee Co! Get a warm drink, a sweet treat, and enjoy the festive ambiance while meeting Mr. Claus.

Foxtail Coffee Co, 276 W. Plant St.

Fridays on the Plaza

Friday, December 13

7:00 pm - 9:00 pm

Holiday Fridays on the Plaza, Holiday performance by Juniper Club

Downtown Winter Garden, Centennial Plaza Gazebo

A Very Merry Farmers Market with Santa Visit

Saturday, December 14

8:00 am - 1:00 pm

Visit with Santa to take photos and share your wish list. Write a letter to Santa and hand deliver it to him. Visit the Festive-decorated market is ideal for shopping for gifts, seasonal décor, as well ass for fresh produce and artisan foods for your holiday celebrations.

Downtown Pavilion, 104 S. Lakeview Avenue

Central Florida Railroad Museum: Free Downtown Walking Tour

Saturday, December 14

8:30 am - 9:45 am

Join us for a 90-minute, one-mile walking tour of downtown Winter Garden while learning the history and impact of the railroads on the community. Meet at the Railroad Museum at 101 S. Boyd Street. Free admission.

Central Florida Railroad Museum, 101 S. Boyd Street

Meet the Grinch

Saturday, December 14

10:00 am - 12:00 pm

Free Event! Celebrate this holiday season by meeting the Grinch! Enjoy sipping on a warm, cozy beverage while getting your photo taken with the cynical grump.

Foxtail Coffee Co, 276 West Plant St.

Art Exhibition: “Reflections of Joy”

Saturday, December 14

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, December 14

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, December 14

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Central Florida Railroad Museum: Railroad Ghost Towns & Phantom Trains

Saturday, December 14

1:30 pm - 3:00 pm

Join historian and author Rick Cronin to learn the history and stories of the forgotten Central Florida ghost towns and railroads. Free admission.

Central Florida Railroad Museum, 101 S. Boyd Street

A Merry Winter Garden Light Show

Saturday, December 14

6:00 pm - 9:00 pm

Spectacular animated holiday-themed light show synchronized to music projected onto the front façade of Winter Garden City Hall. Free.

Winter Garden City Hall, 300 W. Plant Street

Holiday Opera at the Garden

Saturday, December 14

7:00 pm - 8:00 pm

The City of Winter Garden presents HOLIDAY OPERA AT THE GARDEN featuring World-Class Soprano Samar Salamé Hawat. This magical holiday concert is a beautiful blend of classical repertoire with beloved Christmas carols and a great way to make merry memories! Garden Theatre is located in the Holiday Wonderland of historic downtown. Click image to purchase tickets.

Garden Theatre, 160 W. Plant Street

A Merry Winter Garden Light Show

Sunday, December 15

6:00 pm - 9:00 pm

Spectacular animated holiday-themed light show synchronized to music projected onto the front façade of Winter Garden City Hall. Free.

Winter Garden City Hall, 300 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, December 16

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Horse Drawn Holiday Carriage Tours

Monday, December 16

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, December 17

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Reflections of Joy”

Tuesday, December 17

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Tuesday, December 17

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Tuesday, December 17

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Holiday Flix at the Garden

Tuesday, December 17

4:00 pm

Elf movie screening presented by Holiday Flix at the Garden. Enjoy this festive flix in the timeless ambiance of the Garden Theatre while visiting the Holiday Wonderland in historic downtown Winter Garden. Ticket:$5. Click image to purchase!

Garden Theatre, 160 W. Plant Street

Horse Drawn Holiday Carriage Tours

Tuesday, December 17

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, December 18

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Reflections of Joy”

Wednesday, December 18

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Wednesday, December 18

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Wednesday, December 18

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Horse Drawn Holiday Carriage Tours

Wednesday, December 18

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Winter Garden Heritage Museum: Speaker Series with Mike Forrester

Wednesday, December 18

6:30 pm - 8:00 pm

Join Mike Forrester for his presentation of: Winter Garden Then & Now - A Photo Tour of Our Community. A journey through the Winter Garden of yesteryear, compared with photos from today. Free!

Winter Garden Heritage Foundation Heller Hall, 21 E. Plant Street

Holiday Flix at the Garden

Wednesday, December 18

7:00 pm

Elf movie screening presented by Holiday Flix at the Garden. Enjoy this festive flix in the timeless ambiance of the Garden Theatre while visiting the Holiday Wonderland in historic downtown Winter Garden. Ticket:$5. Click image to purchase!

Garden Theatre, 160 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, December 19

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Reflections of Joy”

Thursday, December 19

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Thursday, December 19

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Thursday, December 19

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Horse Drawn Holiday Carriage Tours

Thursday, December 19

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, December 20

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Cocoa & Cookies with Santa Preschool Holiday Program

Friday, December 20

10:00 am - 12:00 pm

Preschoolers 3-5 years old are invited to enjoy a cup of hot cocoa and story time with Mrs. Claus, create a holiday craft, and meet and greet Santa. Hosted by City of Winter Garden Parks & Recreation. Free

Jessie Brock Community Center, 310 N. Dillard Street

Art Exhibition: “Reflections of Joy”

Friday, December 20

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Friday, December 20

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Friday, December 20

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

Fridays on the Plaza

Friday, December 20

7:00 pm - 9:00 pm

Holiday Fridays on the Plaza, Holiday performance Safia Valines

Downtown Winter Garden, Centennial Plaza Gazebo

A Very Merry Farmers Market with Santa Visit

Saturday, December 21

8:00 am - 1:00 pm

Visit with Santa to take photos and share your wish list. Write a letter to Santa and hand deliver it to him. Visit the Festive-decorated market is ideal for shopping for gifts, seasonal décor, as well ass for fresh produce and artisan foods for your holiday celebrations.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “Reflections of Joy”

Saturday, December 21

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street

Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones

Saturday, December 21

11:00 am - 3:00 pm

The four time zones of the United States were created in 1883 by the railroads to standardize schedules and improve safety. This exhibit looks at how the railroads influence the way we schedule our lives, and the tools we use to keep us "on time".

Central Florida Railroad Museum, 101 S. Boyd Street

Winter Garden Heritage Museum: “Seminole Attire: History and Culture through Design”

Saturday, December 21

11:00 am - 3:00 pm

The style of clothing displayed here originated in the 1920s and continues to develop today with its trademark, intricate patchwork designs.

Winter Garden Heritage Museum, 1 N. Main Street

A Merry Winter Garden Light Show

Saturday, December 21

6:00 pm - 9:00 pm

Spectacular animated holiday-themed light show synchronized to music projected onto the front façade of Winter Garden City Hall. Free.

Winter Garden City Hall, 300 W. Plant Street

Holiday Opera at the Garden

Saturday, December 21

7:00 pm - 8:00 pm

The City of Winter Garden presents HOLIDAY OPERA AT THE GARDEN featuring World-Class Soprano Samar Salamé Hawat. This magical holiday concert is a beautiful blend of classical repertoire with beloved Christmas carols and a great way to make merry memories! Garden Theatre is located in the Holiday Wonderland of historic downtown. Click image to purchase tickets.

Garden Theatre, 160 W. Plant Street

A Merry Winter Garden Light Show

Sunday, December 22

6:00 pm - 9:00 pm

Spectacular animated holiday-themed light show synchronized to music projected onto the front façade of Winter Garden City Hall. Free.

Winter Garden City Hall, 300 W. Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, December 23

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Horse Drawn Holiday Carriage Tours

Monday, December 23

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Reservation recommended / fee required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, December 24

7:30 am - 5:30 pm

This exhibition tells the visual story and written narrative of contemporary life in Downtown Winter Garden through the lenses of 10 experienced Crealdé master class students. Black & White photographs highlight Winter Garden's history, its diverse community of residents and business owners, and unique way of connecting historic preservation, economic development, and overall quality of life.

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Art Exhibition: “Reflections of Joy”

Tuesday, December 24

11:00 am - 5:00 pm

This exhibit showcases art that captures the essence of joy. These pieces will radiate positivity, happiness, and the beauty of life, resonating with the warmth and spirit of the season.

Winter Garden Art Association SOBO Art Gallery & Studio, 127 S. Boyd Street