Written by Nancy DeVault and Stephanie Patterson
Winter Garden was incorporated as a town in 1903. Once known for its orange groves and railroad station, this historic suburb in West Orange County is now a favorite among fitness enthusiasts, thanks to the West Orange Trail, and foodies, thanks to new eateries on Plant Street, the main drag lined with quaint shops, coffee shops and eateries. Savor every bite along the way using our culinary map!
Moon Cricket Grille
14 Plant Street, Winter Garden
Long before Crooked Can Brewing Company opened, this saloon-style pub and restaurant housed in a 1912 building impressed beer drinkers with a list of 99 bottle varieties. The goal is to try each kind to earn your name on a placard! Moon Cricket’s signature starter is the Fried Green Tomato, and they claim to have the “best burgers in Winter Garden,” made with a half-pound patty of black Angus beef. Try the Buffalo Chicken Sandwich if you're a sucker for spicy sauce and homemade ranch or blue cheese.
Look closely at the décor as the pine floors, tin ceiling and skylight are original. Orlando natives may recognize light fixtures and brass railings from the former Rosie O’Grady’s on Church Street. Other notable features: wood trimmings made from native trees, stained glass from a local church, and bar and table tops built from bowling lanes. Catch a live band on the interior stage or, for people watching, snag a patio table.
99 W Plant St, Winter Garden
On the eastern end of the Edgewater Hotel building, Thai Blossom has earned its fair share of foodie bragging rights thanks to honors from Orlando Magazine and Orlando Sentinel. While you may associate Thai with spice, the chefs can make almost every dish as hot or as mild as you desire. Consider warming your taste buds with Tom Yum Gai, a traditional hot and sour soup prepared with chicken, chili, lemon grass, galanga and lime juice (or the shrimp alternative); or the Papaya Salad, topped with sliced green papaya, dried shrimp, tomatoes, garlic, peanuts and lime dressing. Dinner specialties range from curry dishes to unique seafood entrees. While not a traditional Thai dessert, the Orange Sunshine Cake is made with 100% Florida OJ, orange mousse, buttercream frosting and yogurt chips. Oh, if you prefer an at-home date night, just call in your take-out order.
Scoops Old Fashioned Ice Cream Store
99 W Plant St, Winter Garden
Nestled in the center of the Edgewater Hotel building, Scoops (once a coffee shop) truly is an old-fashioned shop for two reasons: its ice cream (of course) and its ambiance. Scoops serves up Hershey’s ice cream but it’s not the chocolate company you’re familiar with. The Hershey Creamery Company was founded in 1894 by five Hershey brothers who, oddly enough, had no relation to Milton S. Hershey of the famed Hershey Company. As for the ambiance, stepping through the doorway of Scoops is like stepping back in time. The shop has antique counters, cabinets and décor. You can also order soft serve and add toppings of your choice.
Chef's Table at the Edgewater
99 West Plant Street, Winter Garden
Originally opened in 1927, the Edgewater Hotel is the foundation of Plant Street’s most iconic building. The building's main attraction is The Chef’s Table at the Edgewater, a restaurant offering two dining experiences: The Chef’s Table (upscale) and the The Tasting Room (casual).
Aside from winning numerous local dining awards, The Chef’s Table has been recognized nationally as one of the Top 100 Restaurants in America by Open Table! The intimate tables have views of the kitchen which serves up seasonally-inspired, three-course prix-fixe dinners with optional wine pairings. The Tasting Room offers front of the house seating, plus outdoor patio seating overlooking the iconic foundation. The menu features both cold and hot small plates (the duck fat fries are a must-try!), in addition to mini desserts. Local musicians provide entertainment, and bartenders mix up craft cocktails, beers and wine.
The Whole Enchilada
129 W Plant St, Winter Garden
Owned by brothers Drew and David Cardacci, this Mexican-inspired eatery—which got its start in Fort Lauderdale—boasts a menu of tacos and burritos alongside margaritas made with fresh fruit puree and house sour mix. Don’t skip an order of the guacamole to share, complimented with an assortment of salsas from the downstairs salsa bar. The eats and sips are tasty to be sure, but it’s the restaurant’s laid-back rooftop bar that will keep you coming back. The open-air space is finished with a covered bar, large wooden benches accented with tropical throw pillows, leafy foliage lining the walls, and lawn games.
146 W. Plant St #110, Winter Garden
This colorful neighborhood coffee shop is usually packed to the brim with locals. Sip on a flavored latte (choose from the classics or fun flavors like s’mores or lavender) or an Axum specialty (like the crème brulee, an espresso drink with caramel sauce, vanilla syrup, milk, and a topping of foam and sugar), paired with one of the irresistible desserts or sandwiches. The full drink menu includes the usual suspects, too. Friendly service and delicious coffee make this the perfect haunt for a casual afternoon date. On a nice day, sit outside on the patio and people watch while you sip.
Market to Table Cuisine
146 West Plant Street, Winter Garden
Chef Ryan Freelove upgraded his farmer’s market booth for this delectable modern American restaurant located in the historic Roper building. With a background in farm-fresh, it’s no surprise that Freelove stocks the kitchen with produce from the rooftop greenhouse and local growers like Ocoee-based Bekemeyer Family Farm.
For dinner, plan for a bit of semi-upscale affair. Start with a signature app like the Seafood Tower featuring Maine lobster, shrimp cocktail, oysters, crab claws, and tuna tartare (wowzer!). On a recent date, my husband ordered the filet mignon (sooo tender) with potato puree and red wine jus. Be sure to end the meal on a sweet note by splitting one of the decadent dessert options.
Rosallie Le French Cafe
141 W Plant St, Winter Garden
Escape to Paris, if only for a few hours, when you step inside this charming café amidst the main hustle and bustle of Plant Street. Fresh pastries and tarts tempt from the display case, while quiches, sandwiches and salads serve as heartier lunchtime selections. Caffeinate with one of the café’s signature drinks (the rose mocha is delightful), a classic coffee, or tea served in your own individual French press. For a casual date, head to the back of the café where a fireplace and leather armchairs provide a more intimate, cozy ambiance.
Winter Garden Farmers Market
104 S Lakeview Ave, Winter Garden
This diverse and bustling market located within the heart of Downtown Winter Garden is a favorite among foodies. Snake through multiple rows of vendors sprawled throughout the market tasting everything from homemade marshmallows and pineapple drinks to fresh produce and food truck fare along the way. You'll also find an assortment of local goods, fresh flowers and plants. In between food stops, pull up a seat to enjoy live music near the central pavilion. Find the market outside the downtown pavilion every Saturday morning from 8am-1pm. Read our full guide to the market for tips and favorite vendors.
360 W Plant St, Winter Garden
Date night and top-notch steaks go hand in hand at this family-owned establishment. Expect juicy hand-cut steaks prepared over an oak wood grill, some German-inspired menu items (the family who owns the restaurant is from Germany) upscale digs and a bright, open dining room with views of the bustling kitchen. Come prepared to unplug and connect with one another while savoring a simple, hearty meal. FYI, the restaurant is closed on Mondays.
Plant Street Market
426 W Plant St, Winter Garden
A fixture of Downtown Winter Garden, Plant Street Market is home to an assortment of local vendors and a craft brewery. The cuisine options range from made-to-order mac n’ cheese and acai bowls to BBQ and sushi. A few of our favorites include Michael’s Ali Coal Fired Pizza (share the Brooklyn, topped with melty mozzarella, sausage, rapini and red onion), Crooked Can Brewing Company and Sir Benji’s Donuts. The latter serves up fresh made mini doughnuts with toppings like Oreo cookies and bacon. For an extra romantic afternoon, book a tea social with AntiquiTEAs complete with tiered pastries, a pot of tea each (choose your own infusion), scones, salad, fruit, and veggie sandwich rounds. The tea shop also offers afternoon tea service. Enjoy live music on the weekends on the spacious outdoor patio.
- The Attic Door: Wine bar with regular live music and an intimate atmosphere.
- Pilars: Inviting local cocktail bar with live jazz performances.
- Three Birds Cafe: Laid back cafe hangout for breakfast and lunch.
- Urban Flats: American restaurant with a seasonal menu, cocktails, and weekend brunch.
- Winter Garden Pizza Company: NY-style pizzas served in a relaxed atmosphere.
- Fat Mike's Hot Chicken: Local fast-casual spot for Nashville hot chicken
Feature image credit: Plant Street Market