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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Shop Small Business Saturday 2021
Kick off the holiday shopping season at the annual Downtown Winter Garden Small Business Saturday Sidewalk Sale. Find one-of-a-kind gifts while enjoying special savings in a charming winter wonderland. Stroll and shop the OUTDOOR sale racks in the festive-decorated historic district. There will be also be in-store and online specials and promotions.
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Holiday Moonlight Movie
Grab blankets and chairs and head to a Holiday Moonlight Movie "The Polar Express" under the stars on Saturday, November 27. Preshow activities at 6:30 pm with movie to follow at 7:10 pm. Downtown Pavilion. Free!
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Light Up Winter Garden
Join us on Friday, December 3, from 6:00-9:00 pm, in welcoming 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. Historic Downtown Winter Garden, 300 W. Plant Street.
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Winter Garden Christmas Parade
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!
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Holiday Boutique Stroll
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
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!
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Winter Garden Fire Rescue’s Annual Santa Run
Winter Garden Fire Rescue’s annual “Santa Run” brings Santa and his sleigh through City neighborhoods. The moving parade takes place between 5:45-9:00 pm each as Santa, along with his firefighter, police, and city helpers spread holiday cheer, music, and treats along the way.
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Tis the Season Schedule 2021
Downtown Winter Garden transforms into a winter wonderland with all the holiday trimmings every weekend in December. Click to learn more.
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Dr. Martin Luther King Jr. Community Celebration
Come and celebrate the life and legacy of Dr. King. This community celebration will feature speeches from the community, including those by Dr. King. displays and family friendly activities. food vendors and live stage performers. including a concert throughout the day.
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Moonlight Movie (January 15, 2022)
Head to downtown for a Moonlight Movie to watch Buzz Lightyear, Woody, and their new friend, Forky, in a carnival adventure! Hosted the the City and produced by the Florida Film Academy, Toy Story 4 (G, 100 minutes) will be shown on Saturday, January 15, at the Downtown Pavilion. Preshow activities will include old-fashioned carnival games for the whole family. Bring blankets and chairs and get cozy under the stars. Refreshments will be available to purchase.