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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Winter Garden Fire Rescue Annual SANTA RUN 2022
The Winter Garden Fire Rescue annual “SANTA RUN” brings Santa and his sleigh through neighborhoods within city limits! This moving parade takes place on select nights as Santa -- along with elves of firefighters, police, and City staff-- spread holiday music, treats, and good cheer along the way.
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Tis the Season Schedule 2022
Downtown Winter Garden transforms into a winter wonderland for 38 days of Tis the Season (Dec. 2- Jan. 8). Click to learn more about all the free downtown holiday happenings and the seasonal resident programs to make merry memories!
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Light Up Winter Garden 2022
Join us to welcome the holiday season with this annual event to kick off our 38 days of Tis the Season. The lighting will take place at 6:15 pm at City Hall followed by various activities for all to enjoy. Sponsored by Duke Energy and the City of Winter Garden.
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Winter Garden Christmas Parade 2022
Bring a lawn chair or blanket and head to your favorite spot for this annual event. A long-standing Winter Garden holiday tradition will delight spectators and bring in holiday cheer! Don't forget to look for the Big Guy himself at the end of the parade!
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Christmas Market on Plant Street 2022
Downtown Winter Garden turns into a PEDESTRIAN-ONLY Christmas Market from 1:00 – 5:00 pm on Saturday, December 3. It is the perfect opportunity to enjoy the sights and sounds of the season without cars or traffic.
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Winter Garden Christmas Golf Cart Parade 2022
The 10th Annual Christmas Golf Cart Parade is an amazing sight of elaborately decorated golf carts making their way through historic downtown to spread holiday cheer. Bring a chair or blanket, grab a viewing spot along West Plant Street, and be ready to be amazed.
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Holiday Boutique Stroll (December 8)
Holiday shopping at its finest with a stroll of the boutiques of Downtown Winter Garden to find unique presents while enjoying light refreshments, raffles, outdoor/indoor specials and promotions at participating boutiques.
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De-light-Ful Decorations Contest 2022
Drag out the lights, hang up the garland, put up the glowing Santa and enter your home to win! Festive presentations of outdoor decorations could win up to $100! Winning displays will be posted on the City’s website.
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Dr. Martin Luther King, Jr. Celebration 2023
Commemorate the life and legacy of Dr. Martin Luther King, Jr. with a community celebration! The event includes a parade, a lineup of live music performances, family friendly activities, displays, and food vendors,
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Winter Garden Heritage & Music Festival 2023
Established in 1903, the City of Winter Garden commemorates its heritage with a special 120th anniversary extravaganza. Festivities include five stages of entertainment, strolling performers, and much more! This free event is for all ages.