From retro throwbacks to quaint and charming, Central Florida’s historic downtowns all have their own unique vibe. No doubt Winter Garden’s vibrant downtown has been growing in popularity with millennials and young families over the last decade, and it’s a destination that never disappoints.
Located in the western part of Orange County, Winter Garden’s well-preserved historic district is just 25 minutes from downtown Mount Dora. Originally finding prominence as an orange packing community, the city's picturesque downtown has transformed into a haven for bicyclists, shoppers, diners, families and history buffs.
Visitors will find ample free parking on the streets or within the city's two-story, three-level brick parking garage on Boyd Street. As designed, the spacious new parking garage blends into the historic buildings, so visitors should keep an eye out for directional signs.
Here are some fun things to include while day trippin':
ABOVE: The historic Edgewater Hotel on Plant Street.
Upon arriving downtown, stop inside the small, yet insightful, Winter Garden Heritage Museum on Plant Street, which provides a glance at the rich history of the area. On the same block is the neighboring Central Florida Railroad Museum, which highlights the influence the railroad had in the early development of Florida.
A few steps inside the renovated Edgewater Hotel transports visitors back in time. It’s antique furnishings, fixtures and original 1926 elevator give it the feeling of historic authenticity. Adjacent to its small lobby is an old-fashioned ice cream shop complete with old-school chocolate malts, plus a small-town barber shop reminiscent of downtown Mayberry.
HUGE FARMERS MARKET
ABOVE: The award-winning Winter Garden Farmers Market
On Saturdays from 8 a.m. to 1 p.m., Winter Garden’s award-winning Farmers Market offers up everything from local organic produce, fresh cheeses and chocolate-covered raspberry key lime pie on a stick to live music, handmade items and fresh baked goods. Over the years, this sprawling community market on Lakeview Avenue has reportedly grown to be the largest Farmers Market in Florida and has won numerous awards.
ART & CULTURE LOVERS
ABOVE: The historic Garden Theatre on Plant Street.
Creative types should stroll off Plant Street to the 127 SOBO Art Gallery located in Winter Garden’s original fire station on Boyd Street. The intimate gallery hosts regular new exhibits showcasing area artists and featuring affordably priced original art.
Built in 1935 as a single-screen cinema, the historic Garden Theatre on Plant Street underwent an extensive restoration and reopened in 2008. Inside the Mediterranean revival-style venue, audiences can enjoy a variety of scheduled performances including plays, concerts, movies and dance.
GOOD EATS & LIBATIONS
ABOVE: The Whole Enchilada, one of many downtown eateries.
There are a plethora of excellent dining options on and around downtown’s Plant Street. Rosallie, a casual French bistro, is a must for anyone in need of a stellar cup of joe, craving decadent baked goods, or looking for a good lunch. Axum Coffee is another top spot for a rich morning latte or strong mid-day espresso.
Flavorful lunches and dinners can be found at many downtown eateries, including Melts on Main which dishes out excellent sandwiches and salads for lunch, The Whole Enchilada with its fresh take on Mexican fare and lively rooftop bar, as well as Thai Blossom that features authentic Asian dishes. The Winter Garden Food Tour is the perfect option for visitors who can’t decide on which great restaurant to try. This walking tour takes guests to sample dishes at some of the area’s culinary hot spots while also sharing historical information about the district.
For more upscale dining, The Chefs Table and the Tasting Room are excellent choices located inside the block-long historic Edgewater Hotel. Another option with rave reviews is Market to Table with its modern American cuisine and craft cocktails. Reservations are a good idea at these popular dining establishments.
If you’re looking for stellar live music, a nice glass of wine and cool ambiance, step inside The Attic Door, a casual and swanky wine bar and bistro on Plant Street. Their tasting tower is perfect for sharing and nibbling while sipping your favorite vino.
PLANT STREET MARKET
ABOVE: Crooked Can Brewing at Plant Street Market (photo taken pre-COVID-19)
Located on the edge of downtown and tucked among massive live oaks and winding sidewalks, this popular culinary venue appears as if it’s sat there for generations, but it’s actually a relatively recent addition to Winter Garden. The historic-inspired brick building features approximately 20 vendors offering high-quality food, plus some kiosks selling hand-made items. The Crooked Can Brewing Company, a popular microbrewery and tasting room with an expansive outdoor patio, is also located at Plant Street Market.
ABOVE: Downtown's Splash Pad on Plant Street.
The paved, 22-mile West Orange Trail runs right through downtown Winter Garden, so throwing the bikes in the car makes for a fun weekend adventure. The multi-use trail is built along old railroad alignments and connects the area to downtown Oakland and Apopka to the north. In the warmer months, families can stop at the free downtown Splash Pad to cool off after a long bike ride. Bikes are also available for rental at Bikes and Blades located at mile marker 0 of the West Orange Trail.
HOW TO GET THERE...
Take US 441 South to 429 South and exit on Plant Street. Turn right at the end of the off-ramp and it will take you right into the center of the historic district.