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 (three stages), enjoy special treats, and watch some baseball. Learn how agriculture along with the railroad, Lake Apopka, and baseball were a big part of Winter Garden’s history. Take a trip back in time and learn about a community that came together to be known as Winter Garden.
Discover the city’s history as you take a trip back in time and learn about the community through presentations, interactive programs and displays presented by the Winter Garden Heritage Foundation. In addition to learning about the history of our City, the celebration features numerous activities in the downtown Historic District throughout the day, including five (5) stages featuring high caliber musicians.
In addition to the main stage locations, there will be many of our restaurants and businesses featuring entertainment throughout the day and evening. Beyond the main downtown corridor, there will be family fun day activities (adult and youth) at our Sam Walker Little League and Walker Field Complexes and Veterans Park, including baseball, softball, football, volleyball, soccer, pickle ball, field games, and other children’s activities. 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. A concert will be presented for all to enjoy at the end of the day’s activities.
Brought to you by the City of Winter Garden and the Winter Garden Heritage Foundation and other generous partners.
Plan on spending the day celebrating and enjoying all the festivities.
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 Tree Tour – brought to you by the Bloom and Grow Garden Society and the Winter Garden Heritage Foundation
When: Meet at Winter Garden Heritage Museum at 8:30am on 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 Tree 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 Tree 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 Tree 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
Good Old Fashioned Family Fun for all Ages
- Where: Sam Walker Sports Complex and Veterans 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 pm at the Senior Field
2021 Donut Dash 5K hosted by WGPAL
When: Saturday, November 6, 8:00 am
Where: This year’s Donut Dash 5K will take place in historic Winter Garden as you start and finish at Lake Apopka.
Description: We will have music, kids fun run, t-shirts, medals, Krispy Kreme Donuts, and best donut costume prize.
For more information, visit us at Sommer Sports: www.runsignup.com or please call 407-656-3636 ex. 5416
Bag giveaways by Healthy West Orange
Fall Festival and the Arts – Presented by the Winter Garden Masonic Lodge, Benefiting Local Charities
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. There will also be a silent auction to benefit the local charities here in Winter Garden.
When – Saturday, November 6, 11:00 am to 4:00 pm
Where – The Winter Garden Masonic Lodge, 230 W. Bay Street, Winter Garden
Contact – Karen McGowan by email karenart@yahoo.com
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!
Lawn Games at the Farmers Market
Large family games will be played on the lawn at the Pavilion.
Downtown Pavilion, 104 S. Lakeview Ave.
Saturday, November 6, 10:00 am – 12:00 pm
Music Schedule
There will be five main stages along with small venues throughout Downtown. There will be music from all genres starting at 1 pm and ending at 10 pm.
Headliners include Selwyn Birchwood, Michael Andrew & Swingerhead, Spazmatics, Marlow Rasado and Paint it Black Quartet.
Please check back for the full music schedule.
Downtown Businesses Celebrate our History
Downtown Merchants Celebrate Local History
Businesses will have live music, local art and historic photos on display. Business hours vary.
- Crooked Can Brewing Company/Plant Street Market – live music throughout the day
- The Deli Downtown
- Doxology
- Driftwood Market
- Garden Theatre
- Garden Music School
- Melts on Main
- Pilars Loft
- Plantation Jewelers
- Rosallie Le French Cafe
- Rita’s Italian Ice & Frozen Custard
- Ruby and Rust
- The Sacred Olive
- Shoo Shoo Baby Boutique
- Sweet Dee’s Cupcakery
- The Whole Enchilada
- Writer’s Block Bookstore
- Urban Flats
- Winter Garden Wheel Works
Heritage Activities
Heritage Tree Tour – brought to you by the Bloom and Grow Garden Society and the Winter Garden Heritage Foundation
When: Meet at Winter Garden Heritage Museum at 8:30am Nov 6 with good walking shoes. This will be a 2 mile walking tour that will end at City Hall around 10:30am.
Where: Throughout Downtown
The Bloom & Grow Garden Society working with the City of Winter Garden launched the Winter Garden Heritage Tree 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 Tree 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 Tree 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
Children's Activities
Lawn Games at the Farmers Market
Large family games will be played on the lawn at the Pavilion.
Downtown Pavilion, 104 S. Lakeview Ave.
Saturday, November 6 from 10:00 am – 12:00 pm
Good Old Fashioned Family Fun for all Ages
- Where: Sam Walker Sports Complex and Veterans Park
- When: Festivities begin at 8 am to 5 pm
- Description: Baseball, softball, field games, children’s activities, live music and food for the family
Fall Festival and the Arts – Presented by the Winter Garden Masonic Lodge
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.
Health & Harvest Festival brought to you by Healthy West Orange
- Where: Winter Garden Farmers Market
- When: Saturday, November 6, 8 am – 1 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!
Sponsors & Partners
Presenters
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
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
Purchase an engraved brick to support Winter Garden Heritage Foundation
Purchase an engraved brick at SOBO
Sign up for Volunteer opportunities
Become a Member of the Winter Garden Arts Association
Follow on Social Media:
Sign up to receive Winter Garden Heritage Foundation newsletter
Sign up to receive SOBO newsletter
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