Winter Garden, Florida: Your September Community Guide
Winter Garden, Florida, is renowned for its historic charm and vibrant community spirit. At Corcoran Connect, we believe that a great community is built on shared experiences and local connections. As your trusted real estate concierge, we're thrilled to share this fantastic list of events happening in Winter Garden this September. 🏡💚
Weekly Wonders
Fridays on the PlazaSeptember 5, 12, 19, 26, 20257:00 PM - 9:00 PMCentennial Plaza Gazebo, Historic Downtown
Kick off your weekends with live music! 🎶 Every Friday night, the heart of Historic Downtown Winter Garden comes alive with free live performances at the Centennial Plaza Gazebo. Grab a bite from a local restaurant, find a spot, and enjoy the show!
Winter Garden Farmers MarketEvery Saturday in September8:00 AM - 1:00 PMDowntown Pavilion, 104 S. Lakeview Avenue
A true local gem! 🥕🌻 The award-winning Winter Garden Farmers Market is a must-visit every Saturday. With over 100 vendors, you can find everything from fresh local produce and artisan crafts to beautiful flowers and unique gifts. It's more than a market; it's a community gathering place.
Weekend Gatherings
Handmade By Her MarketSeptember 6, 20254:00 PM - 6:00 PMHome State Brewing Co., 16016 New Independence Pkwy #100
Support local women-owned businesses at this fantastic pop-up market! 🛍️ Enjoy a drink at Home State Brewing Co. while you browse unique, handmade items. It’s a great way to discover new local talent and connect with the community.
Horizon West Cars and CoffeeSeptember 7, 20258:00 AM - 11:00 AM14111 Shoreside Way, Winter Garden, FL
Start your Sunday with some horsepower and caffeine! 🚗☕ This free, family-friendly event welcomes all car and truck enthusiasts. Grab a coffee from Filigree Coffee and check out an amazing collection of vehicles. While you're there, be sure to explore the Homegrown in Horizon West Market for more local finds.
Learn, Grow, and Give Back
Plantocity Plant Propagation ClassSeptember 13, 202511:00 AM - 1:00 PMHome State Brewing Co., 16016 New Independence Parkway #100
Ready to get your hands dirty? 🌿🪴 Learn the secrets of growing your own plants from cuttings at this fun and educational class. It's a perfect opportunity for plant lovers to expand their skills and their indoor garden.
Community Health FairSeptember 17, 202510:00 AM - 2:00 PMCommunity Resource Center, 125 Center Street
Your health is your wealth! 💪 The Community Health Fair offers free screenings for cholesterol, blood pressure, and more. Get vital health information from local experts in a friendly, no-cost setting.
Citizens CPR ClassSeptember 20, 2025Sessions: 9:30 AM - 11:00 AM or 11:30 AM - 1:00 PMFire Department Headquarters Training Room, 1 E. Cypress Street
Gain a life-saving skill! The Winter Garden Fire Rescue Department offers a free, 90-minute CPR class. Learn Hands-Only Adult and Child CPR and proper AED use. Space is limited, so be sure to pre-register online.
Bark, Brunch and BingoSeptember 27, 202511:00 AM - 2:00 PMFoundation for a Healthier West Orange, 1200 E. Plant Street, Suite 200
Support a great cause while having a blast! 🐾 brunch 🐕 This fundraiser for Polka Dogz Pet Rescue includes brunch, bingo, and raffles to help dogs in need. It's a wonderful way to give back and have a fun-filled afternoon.
At Corcoran Connect, we're proud to be part of the Winter Garden community and understand what makes this city a special place to call home. If you're looking to buy or sell a property, remember that we are Your Real Estate Concierge, ready to provide you with a seamless and personalized experience. Let us help you find your perfect home in this wonderful city.