Orlando is the star of Central Florida. But look past the rides, characters, and crowds, and you’ll find five close beaches, the pristine Econlockhatchee River for exploring wetlands, and pretty little towns and lakes surrounding this tourist magnet. One such town is Winter Garden, so called because it was a citrus-growing region that produced fruit when more northern parts of the country were cold in winter. It’s no wonder Winter Garden calls itself “A Charming Little City with a Juicy Past.” Just 20 minutes west of Orlando, Winter Garden is home to more than 40,000 residents who enjoy a walkable downtown filled with shops and restaurants, plus cultural and historic attractions and recreational activities both on land and on Lake Apopka.
Get out on the lake in a kayak or stroll along its shores in Newton Park on the lookout for herons and egrets. The park has a playground and pier from where you can appreciate beautiful sunsets over the state’s fourth-largest lake. The park is close to the Downtown Historic District, which is on the National Registry of Historic Places. Not only are there many things to keep you busy like browsing boutiques, eating a great meal, and, for the kids, cooling off in the splash pad, but you can enjoy it all while surrounded by the beautifully preserved architecture of decades past. Railroad tracks run through the center of the 10-acre district, a reminder of Winter Garden’s early days when the extension of rail lines spurred its initial growth and development.
Exploring downtown Winter Garden, Florida
Downtown Winter Garden is made for strolling. Browse the carefully curated gifts at Driftwood Market or the designer consignment clothes — many never worn — at Gator Lilly’s, which sells Lilly Pulitzer’s colorful clothing. On Saturdays year-round, stop by the Winter Garden Farmers Market for fresh produce, handmade crafts, and artisanal treats.
History buffs will appreciate a visit to the Central Florida Railroad Museum, which offers fascinating insights into the region’s railroading past, and the Winter Garden Heritage Museum, which tells the story of the town’s agricultural history. Both museums are free to enter. Art appreciators will love the town’s street murals and exhibits in the lobby of City Hall and at SOBO Art Gallery, which both highlight the area’s creative talents.
When hunger strikes, The Deli Downtown is beloved for its hearty sandwiches, The Hangry Bison has won awards for its knockout burgers, and Florida chain Bento is a good option for sushi. There are also several choices for upscale dining. Market To Table’s American cuisine includes juicy filet mignon and braised beef short rib as well as a robust wine list, or try the 12-ounce New York strip steak topped with garlic herb butter and à la carte sides at Matthew’s Steakhouse. With a less standard menu of dishes like foie gras and elk chops, Chef’s Table offers several options for each of its three courses and also operates the more casual Tasting Room, with tapas-style dishes and craft cocktails. To sample a variety of local flavors on a food tour, check out the Happy Hour Tour or Saturday Brunch Tour organized by the Winter Garden Heritage Foundation.
Cycling, drinking, and staying the Winter Garden area
