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 destination. Fitness enthusiasts, love West Orange Trail, and foodies love Plant Street, the main drag lined with quaint shops, coffee shops and eateries. Savor every bite along the way using our culinary map!
Updated December 2022 by Dani Meyering
Winter Garden Restaurants on Plant Street
Moon Cricket Grille
14 Plant Street, Winter Garden
mooncricketgrille.com
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.
Thai Blossom Restaurant
99 W Plant St, Winter Garden
mythaiblossom.com
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.
Three Birds Cafe
2 W Plant St, Winter Garden
threebirds.cafe
This laid-back café is a Central Florida favorite for anyone looking to relax and stay awhile. Owner Ashley Morton-Delcourt was born in Paris and raised in Central Florida, and you'll find plenty of French influence in the dining room. The bright, airy space offers plenty of room to lounge, savor conversation with friends, and enjoy a handcrafted coffee or delicious meal.
Three Birds Cafe's menu rotates around fresh, seasonal produce and locally-sourced ingredients, like honey from Clermont hives. In addition to all day breakfast, salads, and savory handhelds, enjoy a selection of specialty coffees, shareable gourmet platters, and beer, wine, and bubbles. The cinnamon toast crunch latte is one of our absolute favorites!
Chef's Table at the Edgewater
99 West Plant Street, Winter Garden
chefstableattheedgewater.com
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 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.
Related: Chef's Table Dining Experiences in Orlando
The Whole Enchilada
129 W Plant St, Winter Garden
twefreshmex.com
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.
Axum Coffee
146 W. Plant St #110, Winter Garden
axumcoffee.com
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.
Related: Coffee Shops in Orlando for True Coffee Lovers
Harrell's Hot Dogs + Cold Cones
54 W Plant Street, Winter Garden
harrellsdogs.com
Craving fast food? Hop over to Harrell's for specialty hot dogs, chicken cones, and ice cream. Hot dogs are fully customizable, from the proteins to the base to the toppings. Choose from all beef or vegan hot dogs, chicken, or bratwurst to start, served on your choice of bun or salad greens. Next, add toppings like caramelized onions or pickled jalapeños, or go bold with bleu cheese crumbles, pineapple, or even Fire Cheetos. Finally, top your creation off with a selection of ten savory sauces. Flavors range from mango habanero mayo to truffle aioli. Even plain old mustard and ketchup get a little flavor boost thanks to added ingredients like ginger, lemon, and garlic.
Complete your meal with sides of fries, mac and cheese, chili or coleslaw, paired with an old-fashioned soda. Order from the takeout window, then take your food to go as you stroll through historic downtown Winter Garden.
Market to Table Cuisine
146 West Plant Street, Winter Garden
market2table.com
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
atelierdining.com/location/rosallie-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.
Buku Vegan at Main House Market
108 South Main Street
mainhousemarket.com
Venture a block or so off of Plant Street and you'll discover Main House Market, a vibrant little haven serving up fresh coffee and kombucha on tap. If Florida artists, crystals, and abundant plant life are your jam, stop by to try a kombucha or coffee flight and grab a bite from Buku Vegan.
Plus, snag incredible plant-based eats from Buku Vegan. Haitan-American Chef Jenny Chicoye is at the helm, serving up a menu of flavorful, Haitian-inspired dishes with a vegan twist. The newly-expanded menu includes Jacmel jackfruit tacos, djon djon rice, and more. Don't miss the new Sunday brunch eats, like Challah bread dredged in spiced coconut milk and topped with berry-lime compote. The market is closed on Mondays.
Winter Garden Farmers Market
104 S Lakeview Ave, Winter Garden
wintergardenfarmersmarket.com
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.
Related: A Guide to Farmers' Markets in Orlando
Matthew's Steakhouse
360 W Plant St, Winter Garden
matthewssteak.com
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, and some German-inspired items (the family who owns the restaurant is from Germany). A bright, open dining room with views of the bustling kitchen creates a lively atmosphere. 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
plantstmarket.com
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. The experience is complete with tiered pastries, a pot of tea each (choose your own infusion), scones, salad, fruit, and veggie sandwiches. The tea shop also offers afternoon tea service. Enjoy live music on the weekends on the spacious outdoor patio.
Related: 7 Quintessential Dates at Plant Street Market
Need to bring along your pup? Discover these Dog-Friendly Restaurants in Winter Garden and Clermont
Also Try:
- The Attic Door: Wine bar with regular live music and an intimate atmosphere.
- Pilars: Inviting local cocktail bar with live jazz performances.
- Urban on Plant Kitchen & Bar: American restaurant with a seasonal menu, cocktails, and weekend brunch.
- Winter Garden Pizza Company: NY-style pizzas served in a relaxed atmosphere.
Feature image credit: Plant Street Market
