Take small-town old Florida charm with its brick-lined streets and stunning architecture, and pair it with culture, food, music, shopping, entertainment… welcome to Winter Garden, Florida. This vibrant community offers anything and everything to locals and visitors alike. Take a day (or take two) to enjoy everything this Central Florida town has to offer… and we’re letting you know, there’s a lot to see, a lot to do, and a lot to eat. So, let’s get down to it.
Winter Garden Restaurants
Foodie or not, if your travels bring you to Winter Garden, this diverse culinary town should be at the top of your taste-bud destinations, as you won’t want to miss these favorite local restaurants:
• Moon Cricket Grille: A vintage grocery store/restaurant and bar located in the historic district of Winter Garden Moon Cricket is a must if you’re in town… trust us. The story behind it is fun and it’s a local favorite. Try their famous Bam-Bam Shrimp.
• Crooked Can Brewery at Plant Street Market: An authentic taproom in the Plant St. Market. A favorite hangout for locals and visitors, Crooked Can is surrounded by charming oak trees, which form a shaded canopy over an artfully designed, red-bricked marketplace buzzing with activity. The attached Plant St. Market has countless food vendors, and food is allowed in the brewery.
• Harry & Larry’s Bar-B-Que: Unique family-run BBQ restaurant, offering an award-winning dine-in and BBQ catering menu. Famous for their mouthwatering smoked BBQ ribs, turkey, brisket and BBQ sandwiches.
• Chefs Table at the Edgewater: World famous and considered “one of America’s Top Restaurants.” Make a reservation for this intimate gourmet dining experience. Local residents rave about it and foodies come from all over the world to sample the superb cuisine and intimate service.
• The Whole Enchilada: Conceptualized by two local brothers with a taste for tacos and a hankering for hot sauce; this fun and friendly dining experience is full of ambiance, personality, wit and “cutting edge” charisma. Choose from a selection of simple yet savory, “no frills” fresh Mex.
Shopping in Winter Garden
One of Central Florida’s premier shopping destinations, Winter Garden invites you to browse through the various downtown shops, museums and art galleries. You’re sure to come away with that perfect gem you just can’t go home without. Check out these spots:
• Plant St. Market: Local indoor artisan market. With almost 20 locally owned and independent businesses, this unique experience is full of diversity, variety and artisan specialties, including natural, organic food and handmade products.
• Historic Downtown Shops: A very engaging and walkable downtown, businesses include antique shops, clothing boutiques, gift shops, home décor, Florida-themed shops and more. The window shopping in downtown Winter Garden is an activity all its own!
• Farmers Market: This community staple offers a large selection of vendors from locally grown produce and baked goods, to homemade soaps and fresh flowers. Pets are welcome and there is live entertainment each week.
West Orange Trail
The 21-mile West Orange Trail, which runs smack-dab through the center of downtown, is paved and packed every day with walkers, runners, cyclists, rollerbladers and more. Make sure you stop and take in the butterfly garden at the Tildenville outpost. Families who venture onto the trail should start in Winter Garden, visit the splash pad, stop at Scoop’s Ice Cream and check out the carved gator bench down the trail in Oakland Park (about a 15-minute walk from downtown Winter Garden – well worth it).
Located in the heart of historic downtown Winter Garden, the Garden Theatre also happens to be on Plant Street. Committed to enriching, engaging and entertaining audiences through creative experiences, the theater hosts live plays, concerts, movies, and more. It showcases an atmospheric theater in a Mediterranean Revival-style venue and is very kid-friendly, hosting summer camps, field trips and an abundance of entertainment specific to children.
Winter Garden Food Tours
The Winter Garden vibe, lush with fantastic cuisine, live music and culture, is deserving of its own food tour. Enter Winter Garden Food Tours, which highlights local Winter Garden and Central Florida grub in a fun and trendy way.
Winter Garden Food Tours provides an opportunity for people to sample sweet and savory food items from multiple restaurant and bakery stops along a downtown Winter Garden walking route. It’s also a great way to meet people and share food experiences with like-minded folks. Mouths… start watering.
Accommodations Near Winter Garden, Florida
There you have it – your one-stop guide to everything you need to know about spending the day in Winter Garden. It’s true the sun shines almost every day of the year here, which makes it super easy to spend your days outside basking in the fun, the food, the fabulousness. When the day is done, come home to Encore Resort at Reunion, just a short drive away. Our guard-gated community features modern, beautifully decorated 4- to 13-bedroom homes with backyard pools, washer/dryer units, and fully equipped kitchens, plus our resort-style amenities like an Aqua Park and free theme park shuttle. Each of our homes offers ample room for you to socialize or relax and unwind, or to plan the week’s activities.