Sneak Preview of the Winter Garden Heritage & Music Festival

Saturday, November 6

8:00 am – 10:00 pm

Downtown Winter Garden & Surrounding Parks

In celebration of Winter Garden’s founding 118 years ago, the City of Winter Garden and the Winter Garden Heritage Foundation will host a daylong celebration of the community’s historic roots with old-fashioned family fun. Exhibits and activities will provide an opportunity to learn about the City’s history, play family-friendly games, listen to live music (five stages), enjoy special treats, and watch some baseball. Take a trip back in time and learn about a community that came together to be known as Winter Garden.

What to Expect

Fall-themed decorations and activities

Winter Garden Masonic Lodge will have a Fall Festival, Children’s Fair and Arts & Crafts Show – starting at 11:00 am

Lawn games at the Farmers Market – 10:00 am – 12:00 pm

Family fun including baseball, softball, football, volleyball, soccer, pickle ball, field games, and children’s activities at Sam Williams Little League Complex and Veterans Memorial Park starting at 8 am – 5 pm

Five stages featuring different genres of music starting in the afternoon

Health & Harvest Festival from 8:00 am – 1:00 pm

Garden Theatre showing of Central Florida Road Trip: Winter Garden

Heritage Displays & Trees Tour

Additional entertainment at many of the Downtown businesses

Come and enjoy a full day of family oriented activities. Stay tuned for details on how to participate, as well as, a complete schedule of activities and entertainment. Brought to you by the City of Winter Garden and the Winter Garden Heritage Foundation and other generous partners.

All day and evening activities on Saturday, November 6, will be held rain or shine. All activities are family-friendly and most are free.

The City of Winter Garden is actively monitoring the incidence of COVID-19 in our region and is following guidance from local health departments and the Centers for Disease Control and Prevention (CDC) regarding gatherings. The City reserves the right to institute necessary changes to these activities to ensure the public health, safety, and welfare of our citizens.

Activities throughout the Day

Heritage Trees Tour 

• When:  Meet at Winter Garden Heritage Museum at 8:30 am November 6, with good walking shoes.  This will be a 2 mile walking tour that will end at City Hall around 10:30 am.
• Where:  Throughout Downtown

The Bloom & Grow Garden Society working with the City of Winter Garden launched the Winter Garden Heritage Trees Project in 2021.  From a list of over 100 trees throughout Winter Garden and with the support of Healthy West Orange and the Winter Garden Heritage Foundation, the “Winter Garden Heritage Trees Walking Tour” was created in the historic district.  This will be a guided walk of 2 miles and 56 trees starting at the Winter Garden Heritage Museum and ending at City Hall on Plant Street.  Labels have been placed on many of the trees with a QR code that allows you to access information about the tree as well as historic information about Winter Garden and its people.  A self guided Heritage Trees Walking Tour brochure will be given to each attendee.  We encourage you to join our tour and meet some of the grand old trees of Winter Garden. 

• Contact: Jim Crescitelli, Winter Garden Heritage Foundation – 407-656-3244

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Good Old Fashioned Family Fun for all Ages 

• Where: Sam Williams Little League Complex and Veterans Memorial Park
• When:  Festivities begin at 8:00 am and end at 4:00 pm
• Description: Baseball, softball, field games, children’s activities, live music and food for the family

Family Concert with Hello Sister starts at 5:00 pm at the Senior Field

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Fall Festival and the Arts 

The Winter Garden Masonic Lodge is hosting the festivities for families with kids of all ages. There will be face painting, games, art, food and lots of family fun! There will be an art show with dozens of local artists.  Don’t forget to take a hay ride with your family or make some fun memories by taking photos in our seasonal photo booth. There will also be a silent auction to benefit the local charities.

• When: Saturday, November 6, 11:00 am to 4:00 pm
• Where: Winter Garden Masonic Lodge No. 165 F&AM, 230 W. Bay Street
  
• Music Schedule:
  • 11:00 am – 11:20 am          Francesca Trio
  • 11:25 am – 11:45 am           Liza Marie Trio
  • 11:50 am – 12:10 pm          Gabriana Trio
  • 12:30 pm – 12:55 pm         Jordan Mohr Trio
  • 1:00 pm – 1:20 pm             Sofia Marangoni Trio
  • 1:25 pm – 1:45 pm              Casey Chillcot Trio
  • 2:00 pm – 4:00 pm            Liza Marie Trio

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Health & Harvest Festival brought to you by Healthy West Orange

• Where:  Winter Garden Farmers Market
• When: Saturday, November 6, 8:00 am – 1:00 pm
• Description:  Enjoy family fun games, fall themed activities, fitness and cooking classes and much more at the annual Health and Harvest Festival brought to you by Healthy West Orange.  There will be complimentary health screenings, music and more!

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Central Florida Railroad Museum

• When: Museum open for visits and tours from 9:00 am – 5:00 pm on Saturday, November 6
• Where: Central Florida Railroad Museum, 101 S. Boyd Street
• Free

Special Presentation by Local Historian

• Description: “The First Train to Winter Garden” presentation by Richard Cronin, local historian
• When: Two Presentations: 11:00 am and 2:00 pm

G-Scale Model Railroad

• Description: G-Scale Model Railroad with controls for kids (and adults) to run
• When: 9:00 am – 5:00 pm

Tours of Library

• Description: Tours of the Museum Library (normally off-limits to visitors)
• When: 9:00 am – 5:00 pm

51^st Anniversary Slide Show

• Description: 51^st Anniversary Slide Show. The Central Florida Railway Historical Society turns 51 this week! Celebrate its evolution through a captioned slide show. (The Central Florida Railroad Museum has spent 38 years right here on Boyd St.)
• When: 9:00 am – 5:00 pm

Special Exhibits and Presentations for the Festival

• Description: Tours and Visits to the Museum. Extra hosts and historians will be on hand to answer questions as you tour the museum during the Festival
• When: 9:00 am – 5:00 pm

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• Description: Broadcast journalist Buddy Pittman hosts a big screen video tour of Winter Garden in a short film that will be playing continuously at the Garden Theatre, the city’s performing arts jewel. Learn about the City’s history, attractions, and year-round activities. Take a break from the festival’s fun as you relax in air conditioned comfort inside this beautiful showplace!
• When: Saturday, November 6, 12:00 pm – 2:00 pm
• Where: Garden Theatre, 160 W. Plant Street
• Free

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Music Schedule

There will be five main stages along with small venues throughout Downtown.  There will be music from all genres starting at 1:00 pm and ending at 10:00 pm.

Headliners include Selwyn Birchwood, Michael Andrew & Swingerhead, Spazmatics, Hello Sister, and Paint it Black Quartet.

LOOP STAGE – 427 W. PLANT STREET

1:00 PM – 2:00 PM:  Dublin Beat Irish Band – Celtic 

3:00 PM – 4:00 PM:  Thomas Wynn and Hannah Harber – American Rock

5:00 PM – 6:00 PM:  Anti Idol – All 90’s Rock

8:00 PM – 9:30 PM:  Selwyn Birchwood – Blues

CITY HALL STAGE – 300 W. PLANT STREET 

11:00 AM – 1:00 PM:  Garden Music School – Various Music

6:00 PM – 8:00 PM:  We Flip Entertainment – Breakdancers

LAKEVIEW STAGE 104 S. LAKEVIEW AVENUE

2:00 PM – 3:00 PM:  Tom Jackson Band – Country

4:00 PM – 5:00 PM: The Gerry Williams Band – Funk, Soul, & R&B

6:00 PM – 7:15 PM: Gamalier Reyes – Salsa & Latin

GAZEBO – 101 W. PLANT STREET

1:00 PM – 2:00 PM:  Porch Dogs – Cajun/Zydeco

3:00 PM – 4:00 PM:  L&G Live – Acoustic Pop, Soft-Rock, 90s Hits

5:00 PM – 6:00 PM:  Molly Holton – Acoustic Blues

8:00 PM – 9:00 PM:  Paint it Black Quartet – Cutting Edge Instrumental 

MAIN STREET STAGE 1 N. MAIN STREET 

11:00 AM – 12:30 PM:  Flight Scene – A Capella Group Country, Top Hits

2:00 PM – 3:00 PM:  Cat Ridgeway and the Tourists – Rock, Soul, Folk

4:00 PM – 5:00 PM:  Bryce Mauldin – Country 

5:00 PM – 7:00 PM:  We Flip Entertainment – Fall Themed Variety Show

7:00 PM – 8:00 PM: Spazmatics – 80s

9:00 PM – 10:00 PM:  Michael Andrew & Swingerhead – Swing/Big Bang

SAM WILLIAMS LITTLE LEAGUE COMPLEX/SENIOR FIELD – 415 S. PARK AVE

3:00 PM – 4:00 PM:  School of Rock – Variety of Kids Rock Musicians 

5:00 PM – 6:00 PM:  Hello Sister – Pop Rock

PILARS LOFT – 146 W. Plant Street

8:00 PM – 11:00 PM:  The After Party at Pilars Loft

Scott Dickinson Jazz Quartet – Contemporary Jazz

SOBO PLAZA STAGE – 127 S. Boyd Street

Sponsored by Pammie’s Sammies

6:00 PM – 8:00 PM: Morrissey Blvd. Band – Cover Band

STROLLING ENTERTAINMENT – HISTORIC DOWNTOWN WINTER GARDEN

2:00 PM – 5:00 PM:  We Flip Entertainment – Fall Themed Strolling Powerskippers 

4:00 PM – 8:00 PM:  Austin Daniels – Strolling Guitarist 

6:00 PM – 9:00 PM:  We Flip Entertainment – Fall Themed Jugglers Strolling 

Please click here for the full music schedule.

Heritage Activities

Heritage Trees Tour 

• When:  Meet at Winter Garden Heritage Museum at 8:30 am November 6, with good walking shoes.  This will be a 2 mile walking tour that will end at City Hall around 10:30 am.
• Where:  Throughout Downtown

The Bloom & Grow Garden Society working with the City of Winter Garden launched the Winter Garden Heritage Trees Project in 2021.  From a list of over 100 trees throughout Winter Garden and with the support of Healthy West Orange and the Winter Garden Heritage Foundation, the “Winter Garden Heritage Trees Walking Tour” was created in the historic district.  This will be a guided walk of 2 miles and 56 trees starting at the Winter Garden Heritage Museum and ending at City Hall on Plant Street.  Labels have been placed on many of the trees with a QR code that allows you to access information about the tree as well as historic information about Winter Garden and its people.  A self guided Heritage Trees Walking Tour brochure will be given to each attendee.  We encourage you to join our tour and meet some of the grand old trees of Winter Garden. 

• Contact: Jim Crescitelli, Winter Garden Heritage Foundation- 407-656-3244

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Outdoor Heritage Display

• When: Saturday, November 6, 8:00 am – 10:00 pm
• Where: Downtown Winter Garden – City Hall
• Free
• Description: The City of Winter Garden and the Winter Garden Heritage Foundation will have outdoor displays that provide the history on some of Winter Garden’s most important historic buildings.

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Central Florida Railroad Museum

• When: Museum open for visits and tours from 9:00 am – 5:00 pm on Saturday, November 6
• Where: Central Florida Railroad Museum, 101 S. Boyd Street
• Free

Special Presentation by Local Historian

• Description: “The First Train to Winter Garden” presentation by Richard Cronin, local historian
• When: Two Presentations: 11:00 am and 2:00 pm

G-Scale Model Railroad

• Description: G-Scale Model Railroad with controls for kids (and adults) to run
• When: 9:00 am – 5:00 pm

Tours of Library

• Description: Tours of the Museum Library (normally off-limits to visitors)
• When: 9:00 am – 5:00 pm

51^st Anniversary Slide Show

• Description: 51^st Anniversary Slide Show. The Central Florida Railway Historical Society turns 51 this week! Celebrate its evolution through a captioned slide show. (The Central Florida Railroad Museum has spent 38 years right here on Boyd St.)
• When: 9:00 am – 5:00 pm

Special Exhibits and Presentations for the Festival

• Description: Tours and Visits to the Museum. Extra hosts and historians will be on hand to answer questions as you tour the museum during the Festival
• When: 9:00 am – 5:00 pm

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Children's Activities

Lawn Games at the Farmers Market

Large family games will be played on the lawn at the Pavilion.

• Where: Downtown Pavilion, 104 S. Lakeview Ave.
• When: Saturday, November 6 from 10:00 am – 12:00 pm

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Good Old Fashioned Family Fun for all Ages 

• Where: Sam Williams Little League Complex and Veterans Memorial Park
• When:  Festivities begin at 8:00 am to 5:00 pm
• Description: Baseball, softball, field games, children’s activities, live music and food for the family

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Fall Festival and the Arts

The Annual Fall Festival is back! The Winter Garden Masonic Lodge is hosting the festivities for families with kids of all ages. There will be face painting, games, art, food and lots of family fun! Don’t forget to take a hay ride with your family or make some fun memories by taking photos in our seasonal photo booth.

• When: Saturday, November 6, 11:00 am to 4:00 pm
• Where: Winter Garden Masonic Lodge no. 165 F&AM, 230 W. Bay Street

 

 

 

 

 

 

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Central Florida Railroad Museum

G-Scale Model Railroad

• Description: G-Scale Model Railroad with controls for kids (and adults) to run
• When: 9:00 am – 5:00 pm

Special Exhibits and Presentations for the Festival

• Description: Tours and Visits to the Museum. Extra hosts and historians will be on hand to answer questions as you tour the museum during the Festival. Also, visit outdoor tent to purchase railroading merchandise.
• When: 9:00 am – 5:00 pm

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Official Event Parking

Corner Lot of Ninth Street and Plant Street (shuttle provided)

848 E. Plant Street

Dillard Street Elementary

311 N Dillard Street (enter from Division Street)

Downtown Parking Garage (3 levels)

160 S. Boyd Street

Downtown Pavilion – Golf Cart (ONLY) Parking

104 S. Lakeview Avenue – Special GOLF CART ONLY parking will be available starting at the conclusion of the Farmers Market.

Public Parking Lot at the corner of S. Dillard Street and E. Plant Street

114 E. Plant Street

Sam Williams Little League Complex

238 W Smith Street (enter from Smith Street)

415 S. Park Avenue (enter from Seminole Street)

Veterans Memorial Park

420 S. Park Avenue (enter from Story Road)

Street Parking, where permissible (Note: Plant Street will be closed on November 6)

Please click here for a parking map.

Presenters/Sponsors/Partners

                             

Builder Sponsors

                                 

                                   

 

Partners

                                       

 

                                             

 

                                            

Support Arts & Culture

How can I show support year-round to the Local Arts?

Winter Garden has many organizations dedicated to arts and culture.  Here are seven ways to support local art in your community.  A good first start to learn about these organizations.    Click on the organizations below to learn more.

1. Donate to a local arts organization

• WG Heritage Foundation
• Garden Theatre
• WG Art Association
• Crealde School of Art – Winter Garden Programming
• Bloom and Grow Garden Society Monarch Butterfly Project

2. Become a member of a local cultural arts organization
3. Attend the array of local events hosted by these organizations
4. Buy local art
5. Support local programs and schools
6. Plan on attending the November 6th celebration – Winter Garden Heritage & Music Festival
7.Become a volunteer for one of these organizations.

Additional Ways to Support Local Arts:

Buy a ticket for Big, the Musical
November 19 – December 19, 2021
Matinee and Evening Performances
Tickets start at $25.  Purchase tickets here

To make a donation to Winter Garden Heritage Foundation please click on the link below.

Donate now!

Sign up for Volunteer opportunities

Become a Member of the Winter Garden Arts Association

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