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
Held every Saturday, the market is a community staple with 100+ vendors offering a large selection items from locally grown produce and baked goods, to homemade soaps and fresh flowers, etc. and even live music.
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Winter Garden Music Festival 2026 - February 21
Historic downtown turns into a mega outdoor concert venue with 30+ live music performances across seven stages. Join us on Sat., Feb. 21, for 11 hours of continuous live music, 11:00 am - 10:00 pm. Free Admission
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Evening at the Pops 2026 - March 28
Enjoy a spring outdoor concert and picnic on the shore of Lake Apopka. Presented by Rotary Club of Winter Garden, with co-sponsorship from the City of Winter Garden.
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Spring Fever in the Garden 2026 - April 11 & 12
The 24th annual, two-day festival transforms downtown's Plant Street into a a celebration of spring with 200+ garden vendors, live entertainment, sidewalk art contest, kids' activities, and more!
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$5 Summer Flix at the Garden 2026
$5 Summer Flix returns to the Garden Theatre on Plant for Summer 2026. A fun and budget-friendly summer outing for all ages! Stay tuned for movie schedule.
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America 250 Events
Winter Garden Celebrates America 250 with community events for all to enjoy: All-American Kids' Parade & Breakfast; Party in the Park & Fireworks Display; Red, White & Blues on the Plaza; Farmers Market Independence Day Celebration; and more!