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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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.
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Shop, Dine & Stroll – March 25, 2023
Spring is the perfect time to stroll the charming historic streets, peruse the outdoor sale racks of the local shops, and take a seat in the expansive outdoor dining areas to enjoy a meal, dessert, or beverage surrounded by colorful spring flowers. SHOP, DINE & STROLL is a fun way to enjoy the nice weather and special sales, as well as live music in the evening.
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Spring Fever in the Garden 2023
Hosted by the Bloom & Grow Garden Society of West Orange County, in conjunction with the City of Winter Garden, the 21st Annual Spring Fever in the Garden is a coveted event for locals and visitors alike. A variety of gardening vendors line the downtown streets with entertainment and activities for all ages to enjoy.
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Arts in April 2023
In celebration of World Art Day, the Winter Garden Art Association and community partners will host a series of events throughout the month of April to raise awareness for local art organizations and artists, while providing opportunities for the community to explore and create art. All of the events are FREE, except for the fundraiser Art Night VIP.