Small Town Charm
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.
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
March 3, 2021
Garden Theatre 160 West Plant Street
March 27, 2021
9:00 am - 9:00 pm
Downtown Winter Garden
In celebration of National Mom and Pop Business Owners Day come shop, dine & stroll Downtown Winter Garden. There will be a sidewalk sale, spacious outdoor dining, plus the farmers market! Many boutiques will be selling spring fashions & merchandise while our restaurants will be having seasonal menus.
March 28, 2021
160 W Plant Street
April 1, 2021
5:30 pm - 8:00 pm
Winter Garden Art Association SOBO Art Gallery & Studio 127 S. Boyd Street