Skip to content

Orlando One Block at a Time: Exploring Winter Garden

Orlando One Block at a Time: Exploring Winter Garden

Castles, Coasters and other attractions tend to dominate the Central Florida landscape and lodge themselves firmly into the minds of visitors. But beyond amusement park maingates and the lush surroundings of resort pools, Orlando is host to many quaint neighborhoods and towns.

Located close to Walt Disney World, Winter Garden has become a hotbed of development for residents who decide to call this corner of the world home. But even though the area has grown by leaps and bounds in the last ten years, central to its charm is Historic Downtown Winter Garden. If you’d like to take a morning or afternoon to explore, here are some great places to check out.

West Orange Trail in Winter Garden Florida
(Courtesy Brooke Fehr)


Plant Street Market in Winter Garden, Florida
(Courtesy Brooke Fehr)

Plant Street Market serves as a food hall and gathering place, and is home to 20 vendors, offering natural, organic and handmade products. With everything from gourmet Mac and Cheese and Pizza to Barbecue and imported Raclette Cheese, there’s something to please every palate. Or, for an upscale farm to table experience, visit Market To Table.

Plant Street Market

426 W. Plant Steet, 407.395.9520

Market To Table

146 W. Plant Steet, 407.395.9871


Ms. Bees in Winter Garden Florida
(Courtesy Brooke Fehr)

The place to see and be seen on Saturday mornings is the award-winning Farmer’s Market with dozens of vendors offering local produce, meat, eggs, honey, plus handmade goods and more. Stop in Ms. Bee’s Gourmet Popcorn and Candy Shoppe to satisfy your sweet and salty cravings, and find one-of-a-kind treasures at Adjectives Market.

Winter Garden Farmer’s Market

104 S. Lakeview Avenue

Ms. Bee’s Gourmet Popcorn and Candy Shoppe

2 E. Plant Street, 407.614.8966


137 W. Plant Street, 321.422.2710


Beer at Crooked Can Brewery in Winter Garden, Florida
(Courtesy Roberto Gonzalez)

Anchoring one end of Plant Street Market is Crooked Can, a homegrown craft brewery that’s among Orlando’s most popular. Grab a beer, plus a bite from the Market, and enjoy the afternoon on one of the outside patios. The Attic Door, a wine bar throughout the week, offers afternoon tea on weekends.

Crooked Can

426 W. Plant Street, 407.395.9520

Attic Door

28 W. Plant Street, 407.750.7063


Railroad Museum in Winter Garden, Florida
(Courtesy Brooke Fehr)

The West Orange Trail, a 20.8-mile rail trail, runs right through the middle of town. BikeThe historic Garden Theatre offers a rich schedule of plays, concerts and movies. Learn more about the area and its history at the Central Florida Railroad Museum.

Garden Theatre

160 W. Plant Street, 407.877.4736

Central Florida Railroad Museum

101 S. Boyd Street, 407.656.0559