Fridays on the Plaza
Come enjoy live music every Friday night on the Plaza in Winter Garden.
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.
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,
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.
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.
Evening at the Pops - March 25, 2023
Bring a blanket or chair and enjoy an outdoor concert under the stars performed by the Space Coast Symphony Orchestra. Newton Park at the shore of Lake Apopka provides a stunning backdrop for this outdoor concert. This is a ticketed event.
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.
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.
Earth Day Events – April 22, 2023
Since 1970, Earth Day is celebrated annually to show support and raise awareness for the protection of our environment. The City of Winter Garden is commemorating Earth Day 2023 with the following community activities.
Downtown Boutique Spring Stroll – May 11, 2023
With Mother’s Day just a few days away, gather friends and family for a special ladies night of SIPS, SNACKS, and SHOPPING in scenic historic downtown. The Downtown Boutique Spring Stroll is the perfect time to take some time to celebrate you and/or the special women in your life.
Memorial Day Community Ceremony - May 29, 2023
The community is invited to a Roll Call of Veterans, placement of wreaths, and patriotic songs to honor and remember our local veterans who gave their lives during times of war or while serving in the United States armed forces. Please come by to pay homage to those that made the ultimate sacrifice.