A picturesque community with a thriving food and culture scene
Winter Garden, Florida, is a charming community of over 48,500 residents west of Orlando. Bordered by Lake Apopka to the north, Winter Garden has a relaxed, suburban feel while also being a desirable place to call home. Winter Garden’s restaurants are second-to-none, while its local gallery and performing arts theater keep the community engaged in the arts.
Residents of Winter Garden love how the town features a number of charming shops and boutiques along its stunning downtown pavilion. Bike and pedestrian-friendly, Winter Garden provides ample opportunities for residents to enjoy activities both indoors and out.
Locals love the laid-back yet energetic feel that Winter Garden has. Though small, Winter Garden has a bustling town square that comes to life on the weekends. A thriving theater, great restaurants, and a well-kept downtown core have helped make Winter Garden the up-and-coming place it is today.
Anyone’s first stop in Winter Garden should be at the Crooked Can Brewing Company and the Plant Street Market. Located within a repurposed warehouse, the indoor market features 20 vendors selling a variety of meats, organic produce, and handcrafted gifts seven days a week, while the Crooked Can Brewing Company is an award-winning brewery that allows you to sip while enjoying live music and a breezy patio.
A favorite restaurant in Winter Garden is Thai Blossom. Start with an order of crispy spring rolls before trying the massaman or green curry as an entree. For dessert, nothing beats the blossom banana delight. Market To Table is a contemporary New American restaurant operated by chef Ryan Freelove, while Chef’s Table is a refined American eatery with a cozy tasting room and great entrees like the ribeye with pear jam and rutabaga puree.
One of the best venues for entertainment in Winter Garden has to be the charming Garden Theatre. Built in the 1930s, the theater was originally a single-room moviehouse before becoming the cornerstone of Winter Garden arts and culture. Now the theater offers year-round productions that often give back to the community. Residents can stop by for their favorite shows or subscribe to season ticket packages. For live music in Winter Garden, locals spend time at spots like Pilars or The Attic Door.
Winter Garden is home to a number of quaint boutiques, including shops like Adjectives and Driftwood Market. Doxology is a favorite for women’s fashion, while Way Chocolate & Coffee is the perfect place to find a sweet treat after dinner. There’s also the incredible Winter Garden Village, where residents can visit over 90 retailers, services, and restaurants.
Taking place right in the heart of the Winter Garden town square, the Winter Garden Farmers Market is a weekly event that brings homegrown produce, meats, herbs, and handmade crafts to residents looking to support local businesses.
To get outdoors and get some exercise, Winter Garden is close to the West Orange Trail, a fantastic 22-mile trail that connects Winter Garden to Oakland and Apopka. Winter Garden has a few golf courses nearby, too, including the Stoneybrook West Golf Club and the Orange County National Golf Center and Lodge.
For indoor activities, Winter Garden is home to the Central Florida Railroad Museum, built from an old 1913 railroad depot. There’s also the fabulous SOBO Art Gallery, which features monthly art exhibitions, open studio space, and classes for the community to take part in.
Explore the 22 miles of walking, jogging, rollerblading, or biking at West Orange Trail. This is an excellent spot for an afternoon of family fun (and exercise!).
The Orange County Public Schools district serves Winter Garden, Florida, and includes the highly-rated ESTEEM Academy. The well-regarded, private Foundation Academy also has a campus in Winter Garden.
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