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

Winter Garden Farmers Market

August 1, 2026
8:00 am - 1:00 pm
Downtown Pavilion - 104 S. Lakeview Avenue (Corner of S. Lakeview Ave & Tremaine St)

Downtown Summer Sidewalk Sale & Live Music

August 1, 2026
9:00 am - 9:00 pm
Downtown Winter Garden

Stroll the historic streets to peruse the summer merchandise closeout deals on all those boutique items that you have been eyeing. Stack your savings with tax-free shopping on items eligible for the Back-to-School Sales Tax Holiday! PLUS, an outdoor live music concert!

Back to School Bash 2026

August 1, 2026
10:00 am - 2:00 pm
Newton Park & Farnsworth Pool, 1 Surprise Drive, Winter Garden

Get the supplies you need to head back to school while enjoying a fun end-of-summer event! Hosted by the City of Winter Garden, this is a FREE family-friendly event for Winter Garden families. Festivities include music with a live DJ, open pool swim, kids' activities, community vendors, refreshments, & free school supplies (which quantities last). Fun for all ages!