A Lakeside Florida City Just Outside Of Orlando Flaunts A Vibrant Walkable Downtown And Upscale Dining

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.

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.

Florida's flat terrain is ideal for bicycling, and Winter Garden residents are lucky to have a 14-foot-wide scenic, paved, car-free trail that begins in their downtown area. Winding 22 miles through towns and over abandoned railroad tracks along the lake from Killarney Station to Apopka Station, the West Orange Trail is one of the best free activities in the Orlando area. Every day you can see cyclists, joggers, inline skaters, and even horseback riders along some stretches. Bike rentals are available in Winter Garden and Killarney to explore this trail. Stops along the route include Tildenville's Butterfly Garden and Oakland Nature Preserve as well as playgrounds in Chapin and Apopka if you're riding with kids.

After your cycle, reward yourself with a cold one at Crooked Can Brewing Company, where you can order the brewery's High Stepper IPA or choose from a number of small-batch and seasonal brews. The brewery is attached to the Plant Street Market, where 20 vendors offer bites from tacos to donuts to mac and cheese to barbecue.

Downtown Winter Garden even has a hotel so you can go ahead and order another beer — you're not driving if you're staying at the Edgewater Hotel. It opened in 1927 with 53 guest rooms renting for $2 to $2.50 per night. Prices have gone up since then, obviously; at the time of writing, you can get a room for over $130 per night. Rooms are on the second and third floors and are decorated with fittingly old-fashioned quilts and floral drapes. Ground floor businesses include a barbershop, ice cream store, and three restaurants. For a more modern stay, Home2 Suites by Hilton Winter Garden has an outdoor pool and charges over $150 per night. Both hotels also offer complimentary breakfast.