Special Events
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Fridays on the Plaza
Come enjoy live music every Friday night on the Plaza in Winter Garden.
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Winter Garden Farmers Market
The Market has quickly grown into a community staple and offers a large selection of vendors from locally grown produce and baked goods, to homemade soaps and fresh flowers, and even live entertainment each week.
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Back to School Bash - August 5, 2023
Back to School Bash Free Backpack & School Supplies Giveaway Saturday, August 5 Get the supplies you need to head back to school while enjoying a fun end-of-summer event! Hosted by the City of Winter Garden, the Back to School Bash is a free family-friendly event for Winter Garden families. The fun, end-of-summer event includes a FREE backpack & school supplies giveaway, free food, an interactive DJ, a foam party, water activities, relay races, community vendors, free limited haircuts by Orlando Technical College-West Campus, and more! Saturday, August 5, 11:00 am - 4:00 pm | Free Zanders Park & Bouler Pool, 362 11th Street Backpack and school supplies giveaway while supplies last. No reservations needed.
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#CityHallSelfie Day -- August 15, 2023
Celebrate Winter Garden’s 120th Anniversary by participating in #CityHallSelfie Day, on Tuesday, August 15, and receive a FREE limited commemorative Winter Garden 120th anniversary tote bag -- a great prop for your selfie! (limited supply)
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Downtown Summer Sidewalk Sale – August 26, 2023
The Downtown Summer Sidewalk Sale is an End-of-Season Clearance Sale with great markdown prices. Now is the time to snag boutique apparel, accessories, home décor, and more at bottom prices! Stroll and shop the OUTDOOR sale racks and tables along the scenic brick-lined streets in historic downtown. Find great deals on all those one-of-a kind items that you have been eyeing, which can only be found at downtown’s unique stores.
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National Night Out Community Event – October 3
National Night Out is a national community-building campaign that promotes police-community partnerships. Millions of neighbors celebrate National Night Out annually across thousands of communities. Please join your community in its celebration.
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Halloween Experience 2023
Halloween is celebrated for 12 days – not just one -- in Winter Garden!
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Health & Harvest Festival 2023 - November 4
Come out to the Health & Harvest Festival at the Winter Garden Farmers Market for FREE wellness activities, health screenings, games, and fun while enjoying the market.
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Craft Affair 2023 - November 11
Arts & crafts lovers will enjoy shopping for one-of-a-kind handmade items at the annual Craft Affair, hosted by the City of Winter Garden Parks & Recreation.
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Small Business Saturday 2023 – November 25
Celebrate Small Business Saturday on November 25 by supporting the independent mom and pop shops that make Winter Garden so special! Small Business Saturday falls on the long, Thanksgiving weekend – perfect timing for holiday shopping while loving local!