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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Halloween Experience 2021
Why celebrate Halloween on one day when the fun can last 10 days! The City’s Halloween Experience, October 22 – 31, provides frightening family-friendly festivities in Downtown Winter Garden, which includes six nights of outdoor animated Halloween Light Shows on City Hall, live music/live shows/pop-up street performers, a hay maze, holiday-themed photo locations, decorations and light displays throughout downtown, merchant themed decorations and food items; a Harvest Sidewalk Sale & Stroll, fall themed Farmers Markets, Halloween movies at the Garden Theatre, plus an outdoor movie for the community and more!
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Halloween Moonlight Movie
Grab some blankets and chairs and get cozy to watch a Moonlight Movie under the stars! The City is presenting Monsters University (2013, G) to the community on Saturday, October 23. Showtime is at 7:10 p.m. but come early for the preshow activities starting at 6:30 p.m. Gather friends and family and meet at the outdoor Downtown Pavilion, 104 S. Lakeview Avenue. Free!
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Harvest Sidewalk Sale & Stroll
Shop the outdoor racks of sale and fall merchandise at the stores of Historic Downtown while enjoying the Halloween Experience decorations and festivities.
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Winter Garden Fall Heritage & Music Festival
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.
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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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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.