Things to Do in Winter Garden, Florida – May 2025 Events Guide

May is blooming with fun in Winter Garden, Florida! Whether you’re looking for live entertainment, family-friendly activities, or unique ways to celebrate Mother’s Day, there’s something for everyone. At Corcoran Connect, we love spotlighting events that bring the community together. Here's your guide to the top happenings around town this month!

🎵 Fridays on the Plaza

Kick off your weekends with live music every Friday night in the heart of Historic Downtown. This free concert series is hosted by the City of Winter Garden and features a rotating lineup of talented performers.

Date: May 9, 16, 23, 30, 2025
Time: 7:00 PM – 9:00 PM
Location: Centennial Plaza Gazebo, Winter Garden, FL 34787
Cost: Free
Music Schedule

🌺 Winter Garden Farmers Market & Mother’s Day Cards Kids' Craft

Visit the award-winning farmers market and let your kids get crafty with homemade Mother’s Day cards at the special Kids' Tent!

Date: May 10, 2025
Time: 8:00 AM – 1:00 PM
Location: Downtown Interactive Fountain & Pavilion, 104 S. Lakeview Avenue, Winter Garden, FL

🎶 Music Bingo @ VFW Winter Garden

Test your musical knowledge and win cash prizes at this lively, public event featuring your favorite hits.

Date: May 11, 2025
Time: 6:00 PM – 8:00 PM
Location: VFW of Winter Garden, 1170 E Plant St, Winter Garden, FL

🧀 Mother’s Day Charcuterie Workshop

Create a stunning, flower-shaped charcuterie board with expert instruction and enjoy 25% off Mother's Day Mimosas while you're at it.

Date: May 11, 2025
Time: 1:00 PM – 3:00 PM
Location: Home State Brewing Co., 16016 New Independence Parkway #100, Winter Garden, FL
Cost: $45

🌿 Winter Garden Farmers Market

Support local vendors and browse over 100 booths selling fresh produce, handmade goods, and more.

Date: May 17, 24, 31, 2025
Time: 8:00 AM – 1:00 PM
Location: Downtown Interactive Fountain & Pavilion, 104 S. Lakeview Avenue, Winter Garden, FL
Event Info

📚 Cookies With A Cop Story Time

Kids can enjoy story time with Winter Garden police officers while snacking on milk and cookies.

Date: May 20, 2025
Time: 10:30 AM
Location: Winter Garden Branch Library, 805 E. Plant Street, Winter Garden, FL

🌪️ Memorial Day Community Celebration

Honor local veterans during this special Memorial Day event hosted by American Legion Post 63 and the City of Winter Garden.

Date: May 26, 2025
Time: 8:30 AM – 9:30 AM
Location: Veteran's Memorial Park, 420 S Park Avenue, Winter Garden, FL
Cost: Free Admission

🍻 Brunch & Drinks Mixology Workshop

Shake up your Saturday with a hands-on cocktail-making class led by Her Velvet Pour. Includes two cocktails and a delicious brunch treat.

Date: May 31, 2025
Time: 10:00 AM – 12:00 PM
Location: Peach Cobbler Factory, 13848 Tilden Road, Winter Garden, FL
Cost: $50 (dessert purchase required)

💚 May is the Month to Explore Winter Garden with Corcoran Connect

From musical evenings and family crafts to workshops and markets, Winter Garden is bursting with things to do this May. As your local real estate experts at Corcoran Connect, we love sharing the events that make our community special. Let us help you find your dream home in a place that always has something happening!

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