Downtown Winter Garden Events

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 1

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Betty J’s Florist 20th Anniversary Celebration

Wednesday, November 1

10:00 am - 4:00 pm

Join Betty J’s Florist in celebrating their 20th Anniversary. Enjoy an outdoor Winter Wonderland set up for the occasion. Free

Betty J’s Florist, 403 S. Dillard Street

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, November 1

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Wednesday, November 1

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, November 2

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Thursday, November 2

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Thursday, November 2

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, November 3

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Friday, November 3

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Friday, November 3

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Fridays on the Plaza

Friday, November 3

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

Health & Harvest Festival at the Winter Garden Farmers Market

Saturday, November 4

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 ~ Hosted by Winter Garden Police Athletic League, Inc.

Saturday, November 4

8:00 am - 11:00 am

(Race starts at 8 am) Run or walk through historic Winter Garden neighborhoods as you start/finish at Lake Apopka. Enjoy live music, sponsor tents, Krispy Kreme donuts, kids fun run, giveaways, prizes, and more! Click image to register.

Newton Park, 1 Surprise Drive

Winter Garden Farmers Market

Saturday, November 4

8:00 am - 1:00 pm

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

Art Exhibition: “Epic Art”

Saturday, November 4

10:00 am - 4:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, November 4

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 6

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 6

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, November 7

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Tuesday, November 7

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Tuesday, November 7

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

SOBO Art Gallery: Technique Tuesday @ 2 PM

Tuesday, November 7

2:00 pm

Weekly “create” event and opportunity for all skills levels to learn, grow, and be inspired through the talents of other artists. Free for members, first-time visitors, and guests of members. Click image for details.

SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 8

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, November 8

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Wednesday, November 8

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, November 9

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Thursday, November 9

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Thursday, November 9

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Jingle ‘n’ Mingle Late Night Shopping Event

Thursday, November 9

5:00 pm - 8:00 pm

Kick off holiday shopping with a fun “Jingle ‘n’ Mingle” shopping event during extended operating hours of 5 – 8 pm at participating stores.

Historic Downtown Winter Garden

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, November 10

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Friday, November 10

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Friday, November 10

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Fridays on the Plaza

Friday, November 10

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 11

8:00 am - 1:00 pm

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

Challenge 22 – 7th Annual Ruck Walk

Saturday, November 11

9:00 am - 4:00 pm

Come out to the Challenge 22 Walk to support the efforts to prevent PTS Suicide of Veterans. There will be Live Music, Food, Raffles, and more, plus a 2.2-mile tribute walk. Click image to register for the walk and/or to donate.

American Legion Post #63, Downtown Winter Garden, 271 W. Plant Street

Art Exhibition: “Epic Art”

Saturday, November 11

10:00 am - 4:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

City of Winter Garden Annual Craft Affair

Saturday, November 11

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

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, November 11

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 13

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Central Florida Railroad Museum – Port of Sanford: Gateway to Middle Florida

Monday, November 13

7:00 pm - 9:00 pm

The November presentation by Rick Cronin will discuss the important role steamboats and railroads serving Sanford played to commerce in the middle of Florida. Visitors are welcomed. Free admission, no reservation required.

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, November 14

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Tuesday, November 14

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Tuesday, November 14

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

SOBO Art Gallery: Technique Tuesday @ 2 PM

Tuesday, November 14

2:00 pm

Weekly “create” event and opportunity for all skills levels to learn, grow, and be inspired through the talents of other artists. Free for members, first-time visitors, and guests of members. Click image for details.

SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 15

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, November 15

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Wednesday, November 15

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, November 16

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Thursday, November 16

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Thursday, November 16

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, November 17

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Friday, November 17

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Friday, November 17

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Fridays on the Plaza

Friday, November 17

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 18

8:00 am - 1:00 pm

Free Thanksgiving craft making at the kids’ tent (Parking Garage Plaza, 9 am – 12 pm), live music, family games on the lawn, and a great place for fresh produce, desserts, décor, and more for your Thanksgiving celebration.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “Epic Art”

Saturday, November 18

10:00 am - 4:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, November 18

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 20

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, November 21

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Tuesday, November 21

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Tuesday, November 21

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

SOBO Art Gallery: Technique Tuesday @ 2 PM

Tuesday, November 21

2:00 pm

Weekly “create” event and opportunity for all skills levels to learn, grow, and be inspired through the talents of other artists. Free for members, first-time visitors, and guests of members. Click image for details.

SOBO Art Gallery & Studio, 127 S. Boyd Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 22

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, November 22

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Epic Art”

Wednesday, November 22

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Wednesday, November 22

7:30 pm

Preview - A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “Epic Art”

Thursday, November 23

12:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Art Exhibition: “Epic Art”

Friday, November 24

11:00 am - 5:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

Fridays on the Plaza

Friday, November 24

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Friday, November 24

7:30 pm

Opening Night - A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Small Business Saturday

Saturday, November 25

Historic Downtown Winter Garden hosts an ALL DAY holiday shopping kick-off event with LIVE MUSIC (11-8 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 25

8:00 am - 1:00 pm

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

Art Exhibition: “Epic Art”

Saturday, November 25

10:00 am - 4:00 pm

From big personalities to big ideas, this exhibit is comprised of 2D & 2D art that makes an Impact. Free Admission

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

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, November 25

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, November 25

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, November 25

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Sunday, November 26

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Sunday, November 26

6:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, November 27

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, November 28

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Tuesday, November 28

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, November 28

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

SOBO Art Gallery: Technique Tuesday @ 2 PM

Tuesday, November 28

2:00 pm

Weekly “create” event and opportunity for all skills levels to learn, grow, and be inspired through the talents of other artists. Free for members, first-time visitors, and guests of members. Click image for details.

SOBO Art Gallery & Studio, 127 S. Boyd Street

Garden Theatre Movie: It’s a Wonderful Life

Tuesday, November 28

7:00 pm

(1946, PG, 2 hr 10 min) - An angel is sent from Heaven to help a desperately frustrated businessman by showing him what life would have been like if he had never existed.

Garden Theatre 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, November 29

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, November 29

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, November 29

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Wednesday, November 29

12:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, November 30

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Thursday, November 30

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, November 30

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Thursday, November 30

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, December 1

7:30 am - 5:30 pm

CAs a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Friday, December 1

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, December 1

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Light Up Winter Garden

Friday, December 1

6:00 pm - 9:00 pm

Welcome the holiday season with this annual 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 Holiday Concert

Friday, December 1

6:30 pm - 8:30 pm

Join us on the front steps of the Historic Downtown First Baptist Church immediately following the Light Up Winter Garden ceremony for a Big Band Christmas Concert, "Christmas In the Garden," featuring Charles Billingsley along with the First Baptist Worship Band and Foundation Academy Steel Drums.

First Baptist Church, 125 E. Plant St.

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Friday, December 1

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Very Merry Farmers Market

Saturday, December 2

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

Art Exhibition: “Mix & Match Mixed Media”

Saturday, December 2

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Winter Garden Christmas Parade

Saturday, December 2

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

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, December 2

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Holiday Market at Downtown

Saturday, December 2

1:00 pm - 4:00 pm

PEDESTRIAN-ONLY outdoor Holiday Market with booths of holiday goods and treats and FREE Entertainment: Dickens Carolers, take-home Holiday Caricatures, Holiday Story Time, & more! W. Plant Street from Woodland Ave. to Lakeview Ave. & S. Main St. Historic Downtown

Historic Downtown

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, December 2

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Create a Gingerbread House ~ Family Event at SOBO Art Gallery

Saturday, December 2

4:00 pm - 5:30 pm

Create a Gingerbread House together – a perfect decoration for the holiday! All materials and step-by-step guidance are provided. $42 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

Saturday, December 2

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

11th Annual Winter Garden Christmas Golf Cart Parade

Saturday, December 2

6:00 pm

The 12th annual holiday parade of elaborately decorated golf carts circles through historic downtown. Grab a good viewing spot along W. Plant Street and enjoy the creativity! Free.

West Plant Street, Historic Downtown

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, December 2

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Sunday, December 3

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Horse Drawn Holiday Carriage Tours

Sunday, December 3

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Sunday, December 3

6:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Merry Winter Garden Light Show

Sunday, December 3

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 4

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, December 5

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Tuesday, December 5

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, December 5

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

SOBO Art Gallery: Technique Tuesday @ 2 PM

Tuesday, December 5

2:00 pm

Weekly “create” event and opportunity for all skills levels to learn, grow, and be inspired through the talents of other artists. Free for members, first-time visitors, and guests of members. Click image for details.

SOBO Art Gallery & Studio, 127 S. Boyd Street

Garden Theatre Movie: Elf

Tuesday, December 5

7:00 pm

(2003, PG, 1 hr 37 min) - Raised as an oversized elf, Buddy travels from the North Pole to New York City to meet his biological father, Walter Hobbs, who doesn’t know he exists and is in desperate need of some Christmas spirit.

Garden Theatre 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, December 6

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, December 6

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, December 6

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Wednesday, December 6

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, December 7

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Thursday, December 7

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, December 7

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Mix & Match Mixed Media” ~ Opening Reception

Thursday, December 7

5:30 pm - 8:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms. Opening Reception. Public Invited. Free Admission.

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

Chanukah Celebration & Menorah Lighting

Thursday, December 7

6:00 pm

All are welcome to join the Chabad of South Orlando for this celebration in honor of the first night of Chanukah. Live band, kids’ crafts, latkes, and more! Fun for the whole family. FREE

Butterfly Sculpture Park, 240 W. Plant Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Thursday, December 7

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, December 8

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Friday, December 8

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, December 8

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

A Merry Winter Garden Light Show

Friday, 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

Holiday Fridays on the Plaza

Friday, December 8

7:00 pm - 9:00 pm

Join Roots & Rosin Duo for this special holiday performance. Free.

Centennial Plaza Gazebo, Historic Downtown

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Friday, December 8

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Very Merry Farmers Market with Santa

Saturday, December 9

8:00 am - 1:00 pm

Visit with Santa (9 am- 12 pm) to take photos and share your wish list. Write a letter to Santa at the KidZone tent and hand deliver it him. Free. The festive-decorated market is ideal for holiday shopping.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “Mix & Match Mixed Media”

Saturday, December 9

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, December 9

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, December 9

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Merry Winter Garden Light Show

Saturday, December 9

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, December 9

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Sunday, December 10

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Horse Drawn Holiday Carriage Tours

Sunday, 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. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Sunday, December 10

6:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Merry Winter Garden Light Show

Sunday, December 10

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 11

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Central Florida Railroad Museum – Central Florida Railfanning Tips and Traps by Danny Harmon

Monday, December 11

7:00 pm - 9:00 pm

The December presentation features railfan video producer Danny Harmon. Danny will share his experiences videotaping the trains of Florida for his Distant Signal YouTube Channel. Visitors are welcomed. Free admission, no reservation required.

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, December 12

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Tuesday, December 12

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, December 12

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

SOBO Art Gallery: Technique Tuesday @ 2 PM

Tuesday, December 12

2:00 pm

Weekly “create” event and opportunity for all skills levels to learn, grow, and be inspired through the talents of other artists. Free for members, first-time visitors, and guests of members. Click image for details.

SOBO Art Gallery & Studio, 127 S. Boyd Street

Horse Drawn Holiday Carriage Tours

Tuesday, 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. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Garden Theatre Movie: The Nightmare Before Christmas

Tuesday, December 12

7:00 pm

(1946, PG, 2 hr 10 min) - The film follows the misadventures of Jack Skellington, Halloweentown’s beloved pumpkin king, who has become bored with the same annual routine of frightening people in the “real world.” When Jack accidentally stumbles on Christmastown, all bright colors and warm spirits, he gets a new lease on life — he plots to bring Christmas under his control by kidnapping Santa Claus and taking over the role. But Jack soon discovers even the best-laid plans of mice and skeleton men can go seriously awry.

Garden Theatre 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, December 13

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, December 13

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, December 13

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Wednesday, December 13

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, December 14

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Thursday, December 14

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, December 14

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Horse Drawn Holiday Carriage Tours

Thursday, December 14

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Thursday, December 14

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, December 15

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Cocoa & Cookies with Santa Preschool Holiday Program

Friday, December 15

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

“Dressing the Part: Selections from the Wardrobe Collection”

Friday, December 15

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, December 15

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Friday, December 15

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Merry Winter Garden Light Show

Friday, 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

Holiday Fridays on the Plaza

Friday, December 15

7:00 pm - 9:00 pm

Join Paint it Black Quartet for this special holiday performance. Free.

Centennial Plaza Gazebo, Historic Downtown

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Friday, December 15

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Very Merry Farmers Market with Santa

Saturday, December 16

8:00 am - 12:00 pm

Due to inclement weather, the Market will operate in a limited capacity with fewer vendors, from 8:00 a.m. to 12:00 p.m.. Visit with Santa to take photos and share your wish list. Write a letter to Santa at the KidZone tent and hand deliver it him. Free. The festive-decorated market is ideal for holiday shopping.

Downtown Pavilion, 104 S. Lakeview Avenue

Central Florida Railroad Museum – Historic Winter Garden Railroad Walking Tour

Saturday, December 16

8:30 am

8:30am start at the Railroad Museum for a 1-mile, 90-minute tour. Free, no registration required.

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Mix & Match Mixed Media”

Saturday, December 16

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Central Florida Railroad Museum – Railroads, Railways and the making of the Tavares and Gulf Legacy

Saturday, December 16

11:00 am

Rick Cronin, museum member, author and historian, will be the presenter. Museum meeting room. Free, no registration required.

Central Florida Railroad Museum, 101 S. Boyd Street

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, December 16

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Central Florida Railroad Museum – Steamboats and Railroads: Florida’s First Transportation Systems

Saturday, December 16

1:30 pm

Thomas Tart, a fifth generation Floridian, historian, Civil War expert, and former Orlando Utilities Commission attorney will be the presenter. Free Admission. No reservation required.

Central Florida Railroad Museum, 101 S. Boyd Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, December 16

2:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Merry Winter Garden Light Show

Saturday, December 16

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, December 16

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Sunday, December 17

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Horse Drawn Holiday Carriage Tours

Sunday, 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. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

A Merry Winter Garden Light Show

Sunday, December 17

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

Orlando Choral Society: The Many Moods of Christmas

Sunday, December 17

6:30 pm

Presented by Orlando Choral Society. The Many Moods of Christmas is a 1963 LP of eighteen Christmas carols by Robert Shaw and famed Broadway orchestrator Robert Russell Bennett. A favorite holiday tradition for families across the Winter Garden area, this concert is designed to inspire, celebrate, and unite us in the spirit of the season. Admission: $10.00 each at the door and a requested toy donation per family for Toys for Tots.

First Baptist Church of Winter Garden, 125 East Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Monday, December 18

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Horse Drawn Holiday Carriage Tours

Monday, 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. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, December 19

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Tuesday, December 19

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, December 19

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

SOBO Art Gallery: Technique Tuesday @ 2 PM

Tuesday, December 19

2:00 pm

Weekly “create” event and opportunity for all skills levels to learn, grow, and be inspired through the talents of other artists. Free for members, first-time visitors, and guests of members. Click image for details.

SOBO Art Gallery & Studio, 127 S. Boyd Street

Horse Drawn Holiday Carriage Tours

Tuesday, 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. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, December 20

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, December 20

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, December 20

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Horse Drawn Holiday Carriage Tours

Wednesday, December 20

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Wednesday, December 20

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, December 21

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Thursday, December 21

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, December 21

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Horse Drawn Holiday Carriage Tours

Thursday, December 21

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Thursday, December 21

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, December 22

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Friday, December 22

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, December 22

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Friday, December 22

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Merry Winter Garden Light Show

Friday, 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

Holiday Fridays on the Plaza

Friday, December 22

7:00 pm - 9:00 pm

Join the Safia Valines Trio for this special holiday performance. Free.

Centennial Plaza Gazebo, Historic Downtown

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Friday, December 22

7:30 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Very Merry Farmers Market

Saturday, December 23

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

Art Exhibition: “Mix & Match Mixed Media”

Saturday, December 23

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, December 23

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Garden Theatre Play: Moonshine & Mistletoe: An Appalachian Christmas Tale

Saturday, December 23

2:00 pm

A wholesome holiday theatrical event for the whole family. The WORLD PREMIERE musical is a nod to a bygone era as the Ballard’s celebrate Christmas with family and friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

A Merry Winter Garden Light Show

Saturday, December 23

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

Dickens Carolers on the Plaza

Saturday, December 23

7:00 pm - 9:00 pm

Join the Dickens Carolers for this special holiday performance. Free.

Centennial Plaza Gazebo, Historic Downtown

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, December 26

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Tuesday, December 26

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, December 26

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Horse Drawn Holiday Carriage Tours

Tuesday, December 26

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, December 27

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Wednesday, December 27

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, December 27

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Horse Drawn Holiday Carriage Tours

Wednesday, December 27

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, December 28

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Thursday, December 28

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, December 28

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Horse Drawn Holiday Carriage Tours

Thursday, December 28

5:30 pm - 9:30 pm

A 20-minute tour experience through festive-decorated and twinkle-lit historic downtown. Provided by Soul Haven Ranch. Fee and reservation required. Click image to book reservation.

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, December 29

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Friday, December 29

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, December 29

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Holiday Fridays on the Plaza

Friday, December 29

7:00 pm - 9:00 pm

Join Gilly & The Girl Duo for this special holiday performance. Free.

Centennial Plaza Gazebo, Historic Downtown

Winter Garden Farmers Market

Saturday, December 30

8:00 am - 1:00 pm

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

Art Exhibition: “Mix & Match Mixed Media”

Saturday, December 30

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

“Dressing the Part: Selections from the Wardrobe Collection”

Saturday, December 30

11:00 am - 3:00 pm

Over the years, the people of West Orange County have donated prom dresses, wedding gowns, sports uniforms, military dress, and more to our Archive. A selection of these treasured items will be presented in this exhibit. Free Admission

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Tuesday, January 2

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, January 2

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, January 2

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Wednesday, January 3

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, January 3

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, January 3

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Thursday, January 4

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, January 4

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, January 4

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “It’s a Wonderful Life in Winter Garden”

Friday, January 5

7:30 am - 5:30 pm

As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the Winter Garden historic downtown district.

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

Modern Day Renaissance: The Winter Garden Story

Friday, January 5

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, January 5

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Fridays on the Plaza

Friday, January 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, January 6

8:00 am - 1:00 pm

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

Art Exhibition: “Mix & Match Mixed Media”

Saturday, January 6

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, January 6

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Reflections of Time II”

Monday, January 8

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Central Florida Railroad Museum – Old Tavares: The Tracks

Monday, January 8

7:00 pm - 9:00 pm

Presenter Mike Ryan will share details of the railroads, and their tracks, that once served Tavares, FL. Free admission, no reservation required.

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “Reflections of Time II”

Tuesday, January 9

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, January 9

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, January 9

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Reflections of Time II”

Wednesday, January 10

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, January 10

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, January 10

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Reflections of Time II”

Thursday, January 11

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, January 11

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, January 11

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Reflections of Time II”

Friday, January 12

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Friday, January 12

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, January 12

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Fridays on the Plaza

Friday, January 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, January 13

8:00 am - 1:00 pm

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

Art Exhibition: “Mix & Match Mixed Media”

Saturday, January 13

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, January 13

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Dr. Martin Luther King Jr. Celebration

Monday, January 15

11:00 am - 4:00 pm

A parade (kick off at 11 am), and celebration (11:30 am – 4 pm) with children’s activities and live music featuring Phoenix 5 and Selwyn Birchwood, Hosted by the City of Winter Garden. Free.

Historic Downtown/Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “Reflections of Time II”

Tuesday, January 16

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, January 16

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, January 16

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Yoga + Meditation at the Boutique: LiveTrends + CFPY

Tuesday, January 16

6:00 pm - 7:00 pm

Event Includes a guided yoga class for all experience levels, guided session on meditation for all experience levels, live plant giveaway. $15. Click image to purchase ticket.

LiveTrends Boutique, 279 Tremaine Street

Art Exhibition: “Reflections of Time II”

Wednesday, January 17

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, January 17

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, January 17

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Reflections of Time II”

Thursday, January 18

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, January 18

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, January 18

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Reflections of Time II”

Friday, January 19

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Friday, January 19

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, January 19

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Fridays on the Plaza

Friday, January 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, January 20

8:00 am - 1:00 pm

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

Art Exhibition: “Mix & Match Mixed Media”

Saturday, January 20

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Central Florida Railroad Museum – Archive Day at the Museum

Saturday, January 20

11:00 am - 3:00 pm

Visit our Library and Archives and see some of the latest additions to our collection.

Central Florida Railroad Museum, 101 S. Boyd Street

Modern Day Renaissance: The Winter Garden Story

Saturday, January 20

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Reflections of Time II”

Monday, January 22

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Art Exhibition: “Reflections of Time II”

Tuesday, January 23

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, January 23

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Tuesday, January 23

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Reflections of Time II”

Wednesday, January 24

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, January 24

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Wednesday, January 24

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Reflections of Time II”

Thursday, January 25

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, January 25

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Thursday, January 25

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Art Exhibition: “Reflections of Time II”

Friday, January 26

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Friday, January 26

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Mix & Match Mixed Media”

Friday, January 26

11:00 am - 5:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Fridays on the Plaza

Friday, January 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, January 27

8:00 am - 1:00 pm

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

Westly’s 7th Annual Virtual/In-Person 5K

Saturday, January 27

8:30 am - 9:30 am

Complete the Virtual 5K In-Person at the Healthy West Orange Fresh Start Zone at Oakland’s Heritage Day. Click image for details about the In-Person 5K or to register for the Virtual 5K (Jan. 1-31).

125 W. Petris Avenue, Oakland

Art Exhibition: “Mix & Match Mixed Media”

Saturday, January 27

10:00 am - 4:00 pm

The craftsmanship of combining mediums is highlighted in 2D and 3D art forms.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, January 27

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Reflections of Time II”

Monday, January 29

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Art Exhibition: “Reflections of Time II”

Tuesday, January 30

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, January 30

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “RetroMod”

Tuesday, January 30

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

LiveTrends Boutique’s Moss Wall Workshop

Tuesday, January 30

6:00 pm - 7:30 pm

Event includes a preserved reindeer moss and materials needed to complete project, step-by-step instructions, light refreshments, customers are welcome to BYOB. $55. Click image to purchase ticket.

LiveTrends Boutique, 279 Tremaine Street

Art Exhibition: “Reflections of Time II”

Wednesday, January 31

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, January 31

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “RetroMod”

Wednesday, January 31

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Thursday, February 1

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, February 1

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “RetroMod”

Thursday, February 1

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “RetroMod” ~ Opening Reception

Thursday, February 1

5:30 pm - 8:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork. Opening Reception. Public Invited. Free Admission.

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

Art Exhibition: “Reflections of Time II”

Friday, February 2

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Friday, February 2

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “RetroMod”

Friday, February 2

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Fridays on the Plaza

Friday, February 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, February 3

8:00 am - 1:00 pm

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

Art Exhibition: “RetroMod”

Saturday, February 3

10:00 am - 4:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, February 3

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

Art Exhibition: “Reflections of Time II”

Monday, February 5

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Art Exhibition: “Reflections of Time II”

Tuesday, February 6

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, February 6

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Tuesday, February 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: “RetroMod”

Tuesday, February 6

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Wednesday, February 7

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, February 7

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Wednesday, February 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

Art Exhibition: “RetroMod”

Wednesday, February 7

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Thursday, February 8

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, February 8

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Thursday, February 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: “RetroMod”

Thursday, February 8

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Friday, February 9

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Friday, February 9

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Friday, February 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: “RetroMod”

Friday, February 9

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Fridays on the Plaza

Friday, February 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

Valentine’s Day Celebration at the Farmers Market

Saturday, February 10

8:00 am - 1:00 pm

Celebrate Valentine's Day with FREE Valentine’s Day craft making at the kids’ tent (Parking Garage Plaza, 9 am – 12 pm), live music, and shopping for Valentine candy, sweets, flowers, and gifts!

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “RetroMod”

Saturday, February 10

10:00 am - 4:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, February 10

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Saturday, February 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: “Reflections of Time II”

Monday, February 12

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Art Exhibition: “Reflections of Time II”

Tuesday, February 13

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, February 13

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Tuesday, February 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: “RetroMod”

Tuesday, February 13

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Wednesday, February 14

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Little Cupid’s Carnival Preschool Holiday Program

Wednesday, February 14

10:00 am - 12:00 pm

Preschoolers 3-5 years old are invited to make Valentine’s Day arts & crafts, play games, face painting, and fun holiday-themed activities. Hosted by the City of Winter Garden Parks & Recreation Dept. Free

Jessie Brock Community Center, 310 N. Dillard Street

Modern Day Renaissance: The Winter Garden Story

Wednesday, February 14

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Wednesday, February 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

Art Exhibition: “RetroMod”

Wednesday, February 14

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Thursday, February 15

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, February 15

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Thursday, February 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: “RetroMod”

Thursday, February 15

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Friday, February 16

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Friday, February 16

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Friday, February 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: “RetroMod”

Friday, February 16

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Fridays on the Plaza

Friday, February 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

Garden Theatre Play: All Shook Up

Friday, February 16

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Winter Garden Farmers Market

Saturday, February 17

8:00 am - 1:00 pm

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

Art Exhibition: “RetroMod”

Saturday, February 17

10:00 am - 4:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, February 17

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Saturday, February 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

Garden Theatre Play: All Shook Up

Saturday, February 17

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: All Shook Up

Saturday, February 17

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: All Shook Up

Sunday, February 18

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “Reflections of Time II”

Monday, February 19

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Art Exhibition: “Reflections of Time II”

Tuesday, February 20

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, February 20

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Tuesday, February 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: “RetroMod”

Tuesday, February 20

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Wednesday, February 21

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, February 21

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Wednesday, February 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

Art Exhibition: “RetroMod”

Wednesday, February 21

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Garden Theatre Play: All Shook Up

Wednesday, February 21

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “Reflections of Time II”

Thursday, February 22

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Take Over The Trails Day

Thursday, February 22

10:00 am - 2:00 pm

Visit community partners along the West Orange Trail for activities, giveaways, and safety info. Click image for more details.

Healthy West Orange Arts and Heritage Center at the Town of Oakland: 126 W Petris Ave, Oakland.

Modern Day Renaissance: The Winter Garden Story

Thursday, February 22

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Thursday, February 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: “RetroMod”

Thursday, February 22

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Garden Theatre Play: All Shook Up

Thursday, February 22

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “Reflections of Time II”

Friday, February 23

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Friday, February 23

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Friday, February 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: “RetroMod”

Friday, February 23

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Fridays on the Plaza

Friday, February 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

Garden Theatre Play: All Shook Up

Friday, February 23

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Winter Garden Farmers Market

Saturday, February 24

8:00 am - 1:00 pm

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

Art Exhibition: “RetroMod”

Saturday, February 24

10:00 am - 4:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, February 24

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Saturday, February 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

Winter Garden Music Festival

Saturday, February 24

11:00 am - 10:00 pm

A multi-stage outdoor concert featuring a variety of entertainment and musical genres performing continuously and simultaneously for 11 hours throughout Downtown Winter Garden. Hosted by the City, you will not want to miss this high caliber entertainment. Free.

Historic Downtown

Garden Theatre Play: All Shook Up

Saturday, February 24

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: All Shook Up

Saturday, February 24

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: All Shook Up

Sunday, February 25

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “Reflections of Time II”

Monday, February 26

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Art Exhibition: “Reflections of Time II”

Tuesday, February 27

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, February 27

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Tuesday, February 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: “RetroMod”

Tuesday, February 27

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, February 28

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Wednesday, February 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

Art Exhibition: “RetroMod”

Wednesday, February 28

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “Reflections of Time II”

Thursday, February 29

7:30 am - 5:30 pm

This exhibition highlights African American artists from Winter Garden and the surrounding areas and demonstrates how their works serve as a testament in preserving time. Curated by Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, this exhibit displays artwork of a variety of disciplines.

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

Garden Theatre Play: All Shook Up

Thursday, February 29

10:00 am

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Modern Day Renaissance: The Winter Garden Story

Thursday, February 29

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Thursday, February 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: “RetroMod”

Thursday, February 29

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Garden Theatre Play: All Shook Up

Thursday, February 29

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “West Orange Women – Making History, Part 2”

Friday, March 1

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Friday, March 1

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Friday, March 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: “RetroMod”

Friday, March 1

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Fridays on the Plaza

Friday, March 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

Garden Theatre Play: All Shook Up

Friday, March 1

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Winter Garden Farmers Market

Saturday, March 2

8:00 am - 1:00 pm

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

Art Exhibition: “RetroMod”

Saturday, March 2

10:00 am - 4:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, March 2

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Saturday, March 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

Garden Theatre Play: All Shook Up

Saturday, March 2

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: All Shook Up

Saturday, March 2

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: All Shook Up

Sunday, March 3

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “West Orange Women – Making History, Part 2”

Monday, March 4

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Tuesday, March 5

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, March 5

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Tuesday, March 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: “RetroMod”

Tuesday, March 5

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Wednesday, March 6

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, March 6

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Wednesday, March 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: “RetroMod”

Wednesday, March 6

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Garden Theatre Play: All Shook Up

Wednesday, March 6

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “West Orange Women – Making History, Part 2”

Thursday, March 7

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, March 7

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Thursday, March 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

Art Exhibition: “RetroMod”

Thursday, March 7

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Garden Theatre Play: All Shook Up

Thursday, March 7

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “West Orange Women – Making History, Part 2”

Friday, March 8

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Friday, March 8

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Friday, March 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: “RetroMod”

Friday, March 8

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Fridays on the Plaza

Friday, March 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

Garden Theatre Play: All Shook Up

Friday, March 8

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Winter Garden Farmers Market

Saturday, March 9

8:00 am - 1:00 pm

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

Farm Day at the Farmers Market

Saturday, March 9

9:00 am - 12:00 pm

All ages will enjoy the visiting Petting Zoo. Get up close with llamas, goats, pigs, chickens, ducks, sheep, cows, and bunnies and learn about the animals’ important contributions on a farm as we celebrate National Farm Day. Petting Zoo: 9 am – 12 pm/Market: 8 am – 1 pm. FREE

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “RetroMod”

Saturday, March 9

10:00 am - 4:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, March 9

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Saturday, March 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

Garden Theatre Play: All Shook Up

Saturday, March 9

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: All Shook Up

Saturday, March 9

7:30 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: All Shook Up

Sunday, March 10

2:00 pm

This hip-swiveling, lip-curling musical fantasy will have you jumpin’ out of your blue suede shoes with Elvis’ hit classics. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “West Orange Women – Making History, Part 2”

Monday, March 11

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Tuesday, March 12

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, March 12

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Tuesday, March 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: “RetroMod”

Tuesday, March 12

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Wednesday, March 13

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, March 13

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Wednesday, March 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: “RetroMod”

Wednesday, March 13

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Thursday, March 14

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

St. Paddle’s Day Winter Garden Community Pickleball Fest

Thursday, March 14

8:00 am

City of Winter Garden Parks & Recreation celebrates 10 years of pickleball by hosting a FREE three-day recreational Pickleball Tournament (March 14-16) for YOUTH & ADULTS. Starts at 8:00 am. Spectators welcome. Registration ends March 8. Also, a free drop-in Clinics & Event on March 16, 12:00-3:00 pm. Free. Click image for details.

Veterans Memorial Park, 420 S. Park Avenue

Modern Day Renaissance: The Winter Garden Story

Thursday, March 14

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Thursday, March 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

Art Exhibition: “RetroMod”

Thursday, March 14

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Friday, March 15

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

St. Paddle’s Day Winter Garden Community Pickleball Fest

Friday, March 15

8:00 am

City of Winter Garden Parks & Recreation celebrates 10 years of pickleball by hosting a FREE three-day recreational Pickleball Tournament (March 14-16) for YOUTH & ADULTS. Starts at 8:00 am. Spectators welcome. Registration ends March 8. Also, a free drop-in Clinics & Event on March 16, 12:00-3:00 pm. Free. Click image for details.

Veterans Memorial Park, 420 S. Park Avenue

Modern Day Renaissance: The Winter Garden Story

Friday, March 15

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Friday, March 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: “RetroMod”

Friday, March 15

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

9th Annual Celtic Festival

Friday, March 15

6:00 pm - 10:00 pm

Crooked Can Brewing Co. presents this celebration of music, food, & culture. Live entertainment includes Todd Nichols solo piper, CDPA Scottish Highland Dancers, FiddleRat, Rosie O’Grady’s Pipe & Drum, stilt walker, face painting. Free admission.

426 W. Plant Street

Fridays on the Plaza

Friday, March 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

St. Paddle’s Day Winter Garden Community Pickleball Fest

Saturday, March 16

8:00 am

City of Winter Garden Parks & Recreation celebrates 10 years of pickleball by hosting a FREE three-day recreational Pickleball Tournament (March 14-16) for YOUTH & ADULTS. Starts at 8:00 am. Spectators welcome. Registration ends March 8. Also, a free drop-in Clinics & Event on March 16, 12:00-3:00 pm. Free. Click image for details.

Veterans Memorial Park, 420 S. Park Avenue

Winter Garden Farmers Market

Saturday, March 16

8:00 am - 1:00 pm

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

Art Exhibition: “RetroMod”

Saturday, March 16

10:00 am - 4:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Central Florida Railroad Museum – Saturday History Series Presentation

Saturday, March 16

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

Modern Day Renaissance: The Winter Garden Story

Saturday, March 16

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Saturday, March 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

9th Annual Celtic Festival

Saturday, March 16

12:00 pm - 10:00 pm

Crooked Can Brewing Co. presents this celebration of music, food, & culture. Live entertainment includes Watters School of Irish Dance, Sara Costello’s School of Irish Dance, Long & Finch, Beemo, Rosie O’Grady’s Pipe & Drum, Mad Science, stilt walker, face painting. Free admission.

426 W. Plant Street

St. Paddle’s Day Winter Garden Community Pickleball Fest

Saturday, March 16

12:00 pm - 3:00 pm

Hosted by City of Winter Garden Parks & Recreation, find out what the pickleball craze is about with free Pickleball Clinics by local instructors and more at this community event! Free.

Veterans Memorial Park, 420 S. Park Avenue

9th Annual Celtic Festival

Sunday, March 17

12:00 pm - 9:00 pm

Crooked Can Brewing Co. presents this celebration of music, food, & culture. Live entertainment includes Sarah Costello’s School of Irish Dance, Blain Curtis, Finnegan Academy of Irish Dance, Rosie O’Grady’s Pipe & Drum, Todd Nichols solo piper, juggler, stilt walker, face painting. Free admission.

426 W. Plant Street

Art Exhibition: “West Orange Women – Making History, Part 2”

Monday, March 18

7:30 am - 4:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Tuesday, March 19

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, March 19

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Tuesday, March 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: “RetroMod”

Tuesday, March 19

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Wednesday, March 20

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, March 20

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Wednesday, March 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: “RetroMod”

Wednesday, March 20

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Thursday, March 21

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, March 21

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Thursday, March 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

Art Exhibition: “RetroMod”

Thursday, March 21

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Friday, March 22

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Friday, March 22

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Friday, March 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: “RetroMod”

Friday, March 22

11:00 am - 5:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Fridays on the Plaza

Friday, March 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

Winter Garden Farmers Market

Saturday, March 23

8:00 am - 1:00 pm

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

Puppet Show at the Farmers Market

Saturday, March 23

9:00 am - 12:00 pm

Sure to capture the hearts of all, Puppet Celebration, Inc. brings their fantastic puppet show to the Winter Garden Farmers Market on SAT. MARCH 23. Enjoy the show as we observe World Puppetry Day. Show: 9 am-12 pm/Market: 8 am- 1 pm. FREE

Downtown Pavilion, 104 S. Lakeview Avenue

Art Exhibition: “RetroMod”

Saturday, March 23

10:00 am - 4:00 pm

Looking back in love and looking forward with excitement as both retro and modern ways of life are represented in 2D and 3D artwork.

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

Modern Day Renaissance: The Winter Garden Story

Saturday, March 23

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Saturday, March 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

Evening at the Pops

Saturday, March 23

6:00 pm

Enjoy an outdoor concert performed by the Space Coast Symphony Orchestra while picnicking under the stars on the shore of Lake Apopka. Bring a blanket or chair. Presented by Rotary Club of Winter Garden, co-sponsor City of Winter Garden. (Rain date: March 24) Click image to purchase ticket.

Newton Park, 31 W. Garden Avenue

Art Exhibition: “West Orange Women – Making History, Part 2”

Monday, March 25

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Art Exhibition: “West Orange Women – Making History, Part 2”

Tuesday, March 26

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Tuesday, March 26

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Tuesday, March 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: “West Orange Women – Making History, Part 2”

Wednesday, March 27

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Wednesday, March 27

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Wednesday, March 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: “West Orange Women – Making History, Part 2”

Thursday, March 28

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Thursday, March 28

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Thursday, March 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

Art Exhibition: “West Orange Women – Making History, Part 2”

Friday, March 29

7:30 am - 5:30 pm

The exhibit highlights two dozen women from the past and the present whose legacy shines today. Presented by the Winter Garden Heritage Foundation.

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

Modern Day Renaissance: The Winter Garden Story

Friday, March 29

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Friday, March 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

Fridays on the Plaza

Friday, March 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

Winter Garden Farmers Market

Saturday, March 30

8:00 am - 1:00 pm

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

Modern Day Renaissance: The Winter Garden Story

Saturday, March 30

11:00 am - 3:00 pm

Winter Garden’s rebirth is presented here in detail so that we may honor the people whose hard work brought about this remarkable story. From mayors to ordinary citizens, people banded together to ensure the preservation of a city that so many of us call home. Free Admission.

Winter Garden Heritage Museum, 1 N. Main Street

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

Saturday, March 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: “High School Top Choice Annual Awards Show”

Monday, April 1

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

Art Exhibition: “High School Top Choice Annual Awards Show”

Tuesday, April 2

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Tuesday, April 2

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

Tuesday, April 2

11:00 am - 5:00 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

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

Tuesday, April 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: “High School Top Choice Annual Awards Show”

Wednesday, April 3

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Wednesday, April 3

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

Wednesday, April 3

11:00 am - 5:00 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

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

Wednesday, April 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: “High School Top Choice Annual Awards Show”

Thursday, April 4

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Thursday, April 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: “Top Choice Fine Arts 10th Annual Awards Show”

Thursday, April 4

11:00 am - 5:00 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

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

Thursday, April 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: “Top Choice Fine Arts 10th Annual Awards Show” ~ Opening Reception

Thursday, April 4

5:30 pm - 8:00 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. Opening reception, Public Invited. Free Admission.

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

Art Exhibition: “High School Top Choice Annual Awards Show”

Friday, April 5

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Friday, April 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: “Top Choice Fine Arts 10th Annual Awards Show”

Friday, April 5

11:00 am - 5:00 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

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

Friday, April 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, April 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

Chalkin’ It Up Sidewalk Art Contest

Saturday, April 6

6:00 am - 4:00 pm

The Bloom & Grow Garden Society presents the annual Chalkin’ It Up Sidewalk Art Contest at Spring Fever in the Garden. Space is limited, registration deadline: March 15. Click image to register.

City Hall, 300 W. Plant Street

Winter Garden Farmers Market

Saturday, April 6

8:00 am - 1:00 pm

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

Kids Arts in April Station at the Farmers Market

Saturday, April 6

9:00 am - 12:00 pm

Hosted by SOBO Art Gallery, come by the Kids Art Tent to create an art activity to celebrate “Arts in April.” Free

Parking Garage Plaza, 160 S. Boyd Street

Spring Fever in the Garden

Saturday, April 6

9:00 am - 5:00 pm

Presented by the Bloom & Grow Garden Society in conjunction with the City of Winter Garden, the 22nd annual two-day festival has a wide array of flowers and foliage for sale, a sidewalk chalk art contest, live music, a Kid Zone, nature-related arts and crafts, and more! Free

Historic Downtown Winter Garden

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

Saturday, April 6

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, April 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

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

Saturday, April 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

Spring Fever in the Garden

Sunday, April 7

10:00 am - 4:00 pm

Presented by the Bloom & Grow Garden Society in conjunction with the City of Winter Garden, the 22nd annual two-day festival has a wide array of flowers and foliage for sale, a sidewalk chalk art contest, live music, a Kid Zone, nature-related arts and crafts, and more! Free

Historic Downtown Winter Garden

Art Exhibition: “High School Top Choice Annual Awards Show”

Monday, April 8

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

Central Florida Railroad Museum – Streamliners into Florida (Part 2)

Monday, April 8

7:00 pm - 8:30 pm

Bill Puckett will discuss some of the passenger trains of the "Streamliner Era" that ran from the 1930s through the 1960s, bringing thousands of passengers to Florida's sunshine for vacations. Visitors are welcome. Free admission, no reservation required.

Central Florida Railroad Museum, 101 S. Boyd Street

Art Exhibition: “High School Top Choice Annual Awards Show”

Tuesday, April 9

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Tuesday, April 9

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

Tuesday, April 9

11:00 am - 5:00 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

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

Tuesday, April 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: “High School Top Choice Annual Awards Show”

Wednesday, April 10

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Wednesday, April 10

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

Wednesday, April 10

11:00 am - 5:00 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

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

Wednesday, April 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: “High School Top Choice Annual Awards Show”

Thursday, April 11

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Thursday, April 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: “Top Choice Fine Arts 10th Annual Awards Show”

Thursday, April 11

11:00 am - 5:00 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

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

Thursday, April 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: “High School Top Choice Annual Awards Show”

Friday, April 12

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Friday, April 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: “Top Choice Fine Arts 10th Annual Awards Show”

Friday, April 12

11:00 am - 5:00 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

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

Friday, April 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, April 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, April 13

8:00 am - 1:00 pm

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

Winter Garden Urban Sketchers Competition

Saturday, April 13

9:00 am - 6:00 pm

Urban Sketchers Competition plus Plein Air Event at the Winter Garden Farmers Market. Free to participate or visit to watch their creations come to life. Free. Check-in starts at 9:00 am.

SOBO Art Gallery, 127 S. Boyd Street

Kids Arts in April Station at the Farmers Market

Saturday, April 13

9:00 am - 12:00 pm

Hosted by SOBO Art Gallery, come by the Kids Art Tent to create an art activity to celebrate “Arts in April.” Free

Parking Garage Plaza, 160 S. Boyd Street

Central Florida Railroad Museum – Archives Day at the Museum

Saturday, April 13

10:00 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

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

Saturday, April 13

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

Central Florida Railroad Museum – Archive Day at the Museum

Saturday, April 13

11:00 am - 3:00 pm

Visit our Library and Archives and see some of the latest additions to our collection.

Central Florida Railroad Museum, 101 S. Boyd Street

West Orange Women: Making History, Part 2

Saturday, April 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

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

Saturday, April 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

“By Request” Jazz Concert presented by the Central Florida Jazz Society

Sunday, April 14

3:00 pm - 5:00 pm

Get ready to sway to the smooth tunes of an amazing jazz trio at our charity concert! Every penny raised goes straight to the Central Florida Jazz Society's Scholarship Fund. Purchase tickets at the door or by clicking image.

Pilars, 146 W. Plant Street

Art Exhibition: “High School Top Choice Annual Awards Show”

Monday, April 15

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

Art Exhibition: “High School Top Choice Annual Awards Show”

Tuesday, April 16

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Tuesday, April 16

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

Tuesday, April 16

11:00 am - 5:00 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

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

Tuesday, April 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: “High School Top Choice Annual Awards Show”

Wednesday, April 17

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Wednesday, April 17

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

Wednesday, April 17

11:00 am - 5:00 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

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

Wednesday, April 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: “High School Top Choice Annual Awards Show”

Thursday, April 18

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Thursday, April 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: “Top Choice Fine Arts 10th Annual Awards Show”

Thursday, April 18

11:00 am - 5:00 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

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

Thursday, April 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

Disney’s Frozen JR. by Lakeview Middle School

Thursday, April 18

6:00 pm

Lakeview Middle School presents Disney Frozen JR., a story of true love and acceptance between sisters with a cast of beloved characters and loaded with magic, adventure, and plenty of humor. A fun event for families and young children. Come meet Elsa and Anna. Tickets are $10 - click image to purchase.

Lakeview Middle School Auditorium, 1200 W. Bay Street

Disney’s Aladdin JR., presented by Sunridge Middle School

Thursday, April 18

7:00 pm

Discover “A Whole New World” with this magically updated version of the Academy Award-Wining Disney classic! Performed by Winter Garden’s Sunridge Middle School students.

Sunridge Middle School Cafetorium, 14955 Sunridge Boulevard

Art Exhibition: “High School Top Choice Annual Awards Show”

Friday, April 19

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Friday, April 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: “Top Choice Fine Arts 10th Annual Awards Show”

Friday, April 19

11:00 am - 5:00 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

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

Friday, April 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

Disney’s Frozen JR. by Lakeview Middle School

Friday, April 19

6:00 pm

Lakeview Middle School presents Disney Frozen JR., a story of true love and acceptance between sisters with a cast of beloved characters and loaded with magic, adventure, and plenty of humor. A fun event for families and young children. Come meet Elsa and Anna. Tickets are $10 - click image to purchase.

Lakeview Middle School Auditorium, 1200 W. Bay Street

Disney’s Aladdin JR., presented by Sunridge Middle School

Friday, April 19

7:00 pm

Discover “A Whole New World” with this magically updated version of the Academy Award-Wining Disney classic! Performed by Winter Garden’s Sunridge Middle School students.

Sunridge Middle School Cafetorium, 14955 Sunridge Boulevard

Fridays on the Plaza

Friday, April 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, April 20

8:00 am - 1:00 pm

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

Kids Arts in April Station at the Farmers Market

Saturday, April 20

9:00 am - 12:00 pm

Hosted by SOBO Art Gallery, come by the Kids Art Tent to create an art activity to celebrate “Arts in April.” Free

Parking Garage Plaza, 160 S. Boyd Street

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

Saturday, April 20

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, April 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

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

Saturday, April 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

Disney’s Aladdin JR., presented by Sunridge Middle School

Saturday, April 20

7:00 pm

Discover “A Whole New World” with this magically updated version of the Academy Award-Wining Disney classic! Performed by Winter Garden’s Sunridge Middle School students.

Sunridge Middle School Cafetorium, 14955 Sunridge Boulevard

Disney’s Aladdin JR., presented by Sunridge Middle School

Sunday, April 21

7:00 pm

Discover “A Whole New World” with this magically updated version of the Academy Award-Wining Disney classic! Performed by Winter Garden’s Sunridge Middle School students.

Sunridge Middle School Cafetorium, 14955 Sunridge Boulevard

Art Exhibition: “High School Top Choice Annual Awards Show”

Monday, April 22

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

Art Exhibition: “High School Top Choice Annual Awards Show”

Tuesday, April 23

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Tuesday, April 23

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

Tuesday, April 23

11:00 am - 5:00 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

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

Tuesday, April 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: “High School Top Choice Annual Awards Show”

Wednesday, April 24

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Wednesday, April 24

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

Wednesday, April 24

11:00 am - 5:00 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

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

Wednesday, April 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: “High School Top Choice Annual Awards Show”

Thursday, April 25

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Thursday, April 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: “Top Choice Fine Arts 10th Annual Awards Show”

Thursday, April 25

11:00 am - 5:00 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

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

Thursday, April 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: “High School Top Choice Annual Awards Show”

Friday, April 26

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Friday, April 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: “Top Choice Fine Arts 10th Annual Awards Show”

Friday, April 26

11:00 am - 5:00 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

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

Friday, April 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, April 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

Garden Theatre Play: Always…Patsy Cline

Friday, April 26

7:30 pm

Opening Night - The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Winter Garden Farmers Market

Saturday, April 27

8:00 am - 1:00 pm

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

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

Saturday, April 27

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, April 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

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

Saturday, April 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

Garden Theatre Play: Always…Patsy Cline

Saturday, April 27

2:00 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Night VIP

Saturday, April 27

6:00 pm - 10:00 pm

Immerse yourself in the arts on this special night that includes a variety of art experiences, beverages, light appetizers, and a silent art auction. This is a ticketed event to benefit the Winter Garden Art Association. $75. Click image to purchase ticket.

Historic Downtown Winter Garden

Garden Theatre Play: Always…Patsy Cline

Saturday, April 27

7:30 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Always…Patsy Cline

Sunday, April 28

2:00 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “High School Top Choice Annual Awards Show”

Monday, April 29

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

Art Exhibition: “High School Top Choice Annual Awards Show”

Tuesday, April 30

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Tuesday, April 30

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

Tuesday, April 30

11:00 am - 5:00 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

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

Tuesday, April 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: “High School Top Choice Annual Awards Show”

Wednesday, May 1

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Wednesday, May 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

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

Wednesday, May 1

11:00 am - 5:00 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

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

Wednesday, May 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

Garden Theatre Play: Always…Patsy Cline

Wednesday, May 1

2:00 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “High School Top Choice Annual Awards Show”

Thursday, May 2

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Thursday, May 2

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

Thursday, May 2

11:00 am - 5:00 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

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

Thursday, May 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

Garden Theatre Play: Always…Patsy Cline

Thursday, May 2

7:30 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “High School Top Choice Annual Awards Show”

Friday, May 3

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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

West Orange Women: Making History, Part 2

Friday, May 3

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

Friday, May 3

11:00 am - 5:00 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

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

Friday, May 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

Fridays on the Plaza

Friday, May 3

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

Garden Theatre Play: Always…Patsy Cline

Friday, May 3

7:30 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Winter Garden Farmers Market

Saturday, May 4

8:00 am - 1:00 pm

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

Shop, Dine & Stroll Plus LIVE MUSIC

Saturday, May 4

10:00 am - 10:00 pm

SHOP the quaint boutiques, DINE al fresco at the scenic patios, and STROLL the picturesque streets while music fills the air with live performances in the center of downtown (Hanger 61, 11am-3pm/Mud Rooster, 4-8pm). Look for the raffle signs at participating stores and restaurants for chances to win free prizes. With Mother’s Day around the corner, the event is a fun way to celebrate – and to shop for -- the special women in your life. Hours vary by merchant.

Historic Downtown Winter Garden

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

Saturday, May 4

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, May 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

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

Saturday, May 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

Garden Theatre Play: Always…Patsy Cline

Saturday, May 4

2:00 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Always…Patsy Cline

Saturday, May 4

7:30 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Always…Patsy Cline

Sunday, May 5

2:00 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Garden Theatre Play: Always…Patsy Cline

Sunday, May 5

6:00 pm

The musical play is full of down-home humor, sincere emotion, and a heart-warming look at a special friendship and includes many of Patsy’s unforgettable hits. Rated PG. Click image to purchase tickets.

Garden Theatre, 160 West Plant Street

Art Exhibition: “High School Top Choice Annual Awards Show”

Monday, May 6

7:30 am - 5:30 pm

Area high school students display top 2D & 3D works of art from SOBO Art Gallery’s 2024 Top Choice High School Annual Awards Show in celebration of Arts in April.

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