70°F
Places to Shop 
Dining and Drinks 
Arts and Entertainment 
Farmers Market 
History and Museums 
Upcoming Events 
Shopping Downtown
Stroll up and down the streets of Historic Downtown Winter Garden and enjoy the one of a kind shops that make Winter Garden an unforgettable experience. No matter what you are looking for, there is a place for you. Bring home a piece of our small-town charm.
Chow Downtown
While taking in the small-town charm as you explore Downtown Winter Garden, make sure to stop in and experience the wonders of our award-winning restaurants.
Discover Fresh Picks at the Farmers Market
Repeatedly voted the best Farmers Market state- and nation-wide, the Market offers a large selection of vendors from locally grown produce, baked goods, specialty foods, to homemade soaps, artisan creations, fresh flowers, and so much more!
Arts and Entertainment
Beyond one of kind shops, award-winning dining experiences, and unforgettable events... Downtown Winter Garden is also home to an underswell of arts, culture, and creativity.
Make History in Downtown Winter Garden
Looking to know more about this charming little city with a juicy past? Visit one of the historic museums located right in the heart of Downtown. Plan a moment of your day to learn how Winter Garden has become a successful example of historic preservation.
Make Time for a Whole Lot of Fun
Whether seeking adventure and new discoveries, or longing to unwind and relax surrounded by historic charm, Downtown Winter Garden has something for everyone. The enchanting small town authenticity turns back time and truly feels like a getaway.
Events You Won't Want to Miss
Winter Garden Farmers Market
November 14, 2026
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)
This award-winning Farmers Market boasts 100 vendors+ offering a variety of goods including farm-fresh produce, artisan crafts, gourmet delights, and much more!
10th Annual Challenge 22 Ruck Walk
November 14, 2026
9:00 am - 12:15 pm
230 W. Bay Street, Winter Garden
Join us for the 10th Annual Challenge 22 Ruck Walk! Walk alongside veterans, families, and supporters as we raise awareness for Post Traumatic Stress and stand together for veteran mental health. Click image to register.
Art Exhibition: “Abstract Conversations”
November 14, 2026
10:00 am - 4:00 pm
SOBO Art Gallery, 127 S. Boyd Street
Annual Craft Affair, hosted by City of Winter Garden
November 14, 2026
10:00 am - 2:00 pm
Jessie Brock Community Center, 310 N. Dillard Street
Discover one-of-a-kind handcrafted treasures including seasonal décor, jewelry, artwork, specialty gifts, and more. With something for every style and budget, shoppers of all ages are welcome to attend. All items are made by talented members of our creative 50+ community.
Living Local. Shop Local. Support local businesses. Learn More