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Small Town Charm
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 Halloween Experience WITH NIGHTTIME ENTERTAIMENT
October 18, 2024
Historic Downtown, 300 W. Plant Street
All Day/Entertainment at Night. City hosts a 14-day family-friendly spooky Halloween Experience throughout Downtown with special live entertainment tonight: Halloween Light Show on City Hall (7-9pm), Street Performers (6-9pm), Hay Maze at City Hall (10am-9pm) Halloween- and Fall-Themed Photo Spots, Outdoor Seasonal Decorations & Light Displays, and more!
Art Exhibition: “¡Viva El Arte!”
October 18, 2024
7:30 am - 5:30 pm
Art in Public Places Gallery in City Hall, 300 W Plant Street
Halloween Spooktacular Preschool Program
October 18, 2024
10:00 am - 12:00 pm
Jessie Brock Community Center, 310 North Dillard Street
Central Florida Railroad Museum – It’s About Time: How The Railroads Created Our Time Zones
October 18, 2024
11:00 am - 3:00 pm
Central Florida Railroad Museum, 101 S. Boyd Street
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