Downtown Winter Garden

Small Town Charm

Places to Shop

Dining and Drinks

Arts and Entertainment

Farmers Market

History and Museums

Upcoming Events

Family enjoying a day of shopping in Winter Garden

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.

View Shops

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.

Foodies Paradise Here

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!

Get Pickin'

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.

Culture this way

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.

Explore History

Children Playing in the Downtown Interactive Fountain

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.

Places to Play

Events You Won't Want to Miss

Art Exhibit: “Tempest & Tornadoes” at City Hall

October 23, 2026
7:30 am - 5:30 pm
Winter Garden City Hall Art in Public Places Gallery, 300 W. Plant Street

Curated by the Winter Garden Heritage Foundation, the exhibition includes photographs and documents detailing extreme weather events that West Orange County and its people have endured over the past 130 years, which have had a part in shaping the region.

Grand Opening/Ribbon Cutting Ceremony: Tucker Ranch Holistic Health & Wellness Park and Botanical Garden

October 23, 2026
10:00 am
100 Avalon Road, Winter Garden

Join the City of Winter Garden for a ribbon cutting ceremony to open the 25.6-acre crown jewel park and gardens within Tucker Ranch to the public. Be one of the first to see and take a tour of Central Florida's new oasis! Free

Halloween Spooktacular Preschool Holiday Event

October 23, 2026
10:00 am - 12:00 pm
Jessie Brock Community Center, 310 N. Dillard Street

Put on your favorite costume and join the City of Winter Garden Parks & Recreation Department for a festive morning of Halloween fun, including carnival-style games with prizes, holiday-themed crafts, snacks, and music. Costumes encouraged! For ages 3 -5 years old. Free.