Things to Do in Winter Garden, Florida – August 2025 Events & Activities
Looking to soak up the last bits of summer before school starts? Winter Garden, Florida, is packed with family fun, live music, local food, back-to-school celebrations, and more this August! Whether you're exploring as a local or visiting to get a feel for the community, Corcoran Connect has you covered with this exciting lineup of events.
🎶 Fridays on the Plaza
Date: August 1, 8, 15, 22, 29
Time: 7:00 PM – 9:00 PM
Location: Centennial Plaza Gazebo, Historic Downtown
Cost: Free
Live music every Friday night at the Plaza makes for a perfect way to kick off the weekend. Grab a bite from a local restaurant and enjoy the sounds of talented musicians in a charming downtown setting.
🥕 Winter Garden Farmers Market
Date: August 2, 9, 16, 23, 30
Time: 8:00 AM – 1:00 PM
Location: Downtown Pavilion, 104 S. Lakeview Avenue
A community favorite and a must-visit! With over 100 vendors offering everything from fresh produce and local honey to artisan crafts and handmade jewelry, this market is a true reflection of Winter Garden's community spirit.
🛍️ Downtown Summer Sidewalk Sale & Live Music
Date: Saturday, August 2
Time: 9:00 AM – 8:00 PM
Location: 300 W. Plant Street
Enjoy major end-of-summer discounts from downtown shops, live music at Centennial Plaza, and fun for the kids—including a free treat and a Back-to-School Kids’ Craft at SOBO Art Gallery (9 AM–1 PM).
🎒 Back to School Bash 2025
Date: Saturday, August 2
Time: 11:00 AM – 4:00 PM
Location: Zanders Park & Bouler Pool, 362 11th Street
Cost: Free
Celebrate the new school year with water activities, foam fun, an interactive DJ, and more. Free backpacks and school supplies will be given away while supplies last. Hosted by the City of Winter Garden.
🎬 Summer Flix at the Garden – Lilo & Stitch
Date: Tuesday, August 5
Time: 10:00 AM
Location: Garden Theatre, 160 W. Plant Street
Enjoy a morning movie for just $5! Kids 12 and under get free popcorn, making this an affordable and fun family outing.
🐶 Bone Voyage
Date: August 7
Time: 6:30 PM – 9:30 PM
Location: Plant Street Market
Wish the soon-to-be service dogs well as they move on to professional training. Celebrate with good food and great company at this heartfelt send-off at Plant Street Market.
🍦 Back to School Ice Cream Social – The Nest Schools
Date: August 8
Time: 5:00 PM – 6:00 PM
Location: The Nest Schools Winter Garden, 16161 Marsh Rd
Meet the teachers, tour the school, and learn about their unique outdoor play spaces while enjoying ice cream with the family!
🧸 Teddy Bears Picnic
Date: August 13
Time: 7:00 AM – 10:00 AM
Location: Newton Park Polytunnels and Gardens, 31 W Garden Ave
A whimsical morning of storytelling, crafts, birdwatching, and more! Bring your lunch, your favorite teddy, and your imagination. Children under 8 must be accompanied by an adult.
🦞 Rockstar Lobster Food Truck
Date: August 14
Time: 5:00 PM – 8:00 PM
Location: 6151 Lake Lodge Drive
Craving seafood? Grab a lobster roll or try lobster fries and fried lobster bites. Non-seafood options like loaded cheeseburger fries and mac n’ cheese bites will also be available.
🚗 Cars and Coffee Winter Garden
Date: August 23
Time: 8:00 AM – 10:30 AM
Location: Longhorn Steakhouse, 3118 Daniels Rd
Cost: Free
A paradise for car lovers! Whether you're into exotics, muscle cars, or customs, come mingle with other enthusiasts and see some amazing rides.
🚲 Golf Cart & Bicycle Registration
Date: August 29
Time: 2:00 PM – 4:00 PM
Location: Winter Garden Police Department, 251 W. Plant Street
The Winter Garden Police Department offers a chance to register your golf cart or bicycle—essential for recovery in the case of theft.
Why Corcoran Connect Loves Winter Garden
At Corcoran Connect, we’re more than real estate experts—we’re locals who care about the community. We love seeing Winter Garden come alive with music, markets, and family-friendly events like these. If you're thinking about buying or selling a home in the area, we're here to help you make the move confidently.
Let Corcoran Connect guide you through Winter Garden—your future home might just be waiting among the charm, community, and connection this city has to offer.