9 Amazing Experiences In Beautiful Winter Garden, Florida

Winter Garden, Florida, is a charming historic village that has experienced an incredible re-birth. In fact, there is so much to do that one visit may not be enough. Thirty minutes west of downtown Orlando, a stop in this former citrus town established in 1908 is well worth your time.

Downtown Winter Garden is listed on the National Register of Historic Places due to the incredible architecture preserved and repurposed. Today, the old storefronts house eateries and trendy shops. As you stroll along Plant Street, you’ll admire the streetscape that looks like part of a movie set. Flowers are everywhere in pots and on trellises, like the trailing wisteria vines adorning a pergola in the center of the thorofare. Under the wisteria, a gorgeous seating area offers a great place to relax and enjoy the scenery. The award-winning West Orange Trail has over 20 miles of biking lanes and will soon become part of the 250-mile Coast to Coast Connector Trail. It runs through Winter Garden, which sits along the fourth largest lake in Florida, Lake Apopka. If you love to shop, dine, bike, sip award-winning craft beer, or enjoy a beautiful sunset, here are nine reasons (in no order) to stop in beautiful Winter Garden, Florida.

Crooked Can Brewery (Photo Credit: Jeanine Consoli)

1. Sip Award-Winning Craft Beer

The Crooked Can Brewing Company is a beer-lover’s dream. This local Florida brewery produces delicious craft brews, fulfilling a mission to provide visitors and fans a great reason to drink locally. The brewmasters use cutting-edge brewing practices and blend old-world techniques to create a tempting full-bodied beer list. The “Core Brands” include an IPA, a Hefeweizen, and the award-winneing Florida Sunshine Lager. Still, you can check the website to see what’s on tap when you’re in town, including seasonal and small-batch varieties. This state-of-the-art brewing facility is linked with the vendor hall known as Plant Street Market, so it’s easy to pair a pint with fresh organic food. The outdoor patio is draped in Spanish moss from the stately Live Oak trees. It’s a perfect place to sip away a few hours while you sample all the incredible food from the Plant Street Market vendors. If you want to experience how the “magic” is made, tours are available on Sundays from 12–4 p.m. every hour.

shops along Plant Street (Photo Credit: Visit Orlando)

2. Taste Delicious Cuisine At Plant Street Market

Plant Street Market is an indoor artisan’s market and food hall. The vendor stalls are in a building attached to the Crooked Can Brewing Company. The proximity of delicious world cuisine makes for an incredible dining experience. Pair your foodie finds with a Crooked Can craft beer from the brewer and walk around the market to sample natural, organic foods and shop for goods from over 20 vendors. Specialty chocolates, pastries, donuts, and ice pops are tempting treats after your meal. The market is open 7 days a week. This is a fun place to bring your pet and relax while listening to live music on the patio. There are even specialty coffee and artisan tea stalls, which make for a tasty mid-day pick-me-up. I loved sampling from different shops and enjoyed empanadas, tacos, and pizza on my first trip. It was fantastic, and I can’t wait to head back for more.

Jeanine Consoli

3. Bike The West Orange Trail

The West Orange Trail is 20.8 miles of paved trail stretching through Winter Garden, paralleling the southeastern shore of gorgeous Lake Apopka. This free amenity makes Winter Garden an official Florida Trail Town. The smooth surface is perfect for biking, hiking, rollerblading, and birding while enjoying the natural setting. The path winds you into town and is great for scoping out the antique stores and eateries, especially when you need a refreshment. If you’re biking with children, you can make a pit stop at one of the several playgrounds along the way. The West Orange Trail is Orlando’s longest paved trail, and if you didn’t bring your bike, you could rent one from West Orange Trail Bikes & Blades Co. They’ll deliver a bicycle to your location for an extra fee. They have kid-sized bikes and bike trailers for those too young to pedal, and they offer tour packages that could take 2 hours or longer depending on what you want to see and how far you’d like to go.

Jeanine Consoli

4. Adore An Epic Sunset At Lake Apopka

If you like to fish, you’ll find some of the biggest bass anywhere swimming around Lake Apopka. The fourth-largest lake in Florida, at over 30,000 acres, was once considered a “dead lake” due to phosphates poisoning the fish and causing algae bloom. But thankfully, that’s changed. Efforts to clean the lake from runoff and the natural spring that feeds and refreshes the water have made it safe for boating, kayaking, canoeing, and fishing. If you aren’t an angler but love to watch a beautiful sunset, drive to Newton Park before the orange ball dips into the water. You can relax, picnic, and enjoy the view.

Visit Orlando

5. Shop At The Winter Garden Farmers Market

The Winter Garden Farmers Market is a weekly event where farmers and artisans offer their produce and products. Every Saturday from 8 a.m.–1 p.m. year-round, vendors sell their items in the city pavilion on Tremaine Street. Start your day at the market and then continue shopping at the many bespoke retailers around the historic downtown. You’ll discover fresh produce, plants, crafts, and specialty foods at the Farmers Market.

Jeanine Consoli

6. Enjoy The Performing Arts At The Garden Theater

The Garden Theater has graced Plant Street since 1935 as a single-screen cinema. Today, it functions as “the premier performing arts center in West Orange County.” You’ll enjoy more than 200 professional events each season, including live theater, concerts, dance performances, and films. The building, constructed in the Mediterranean Revival style, was renovated over the years for other uses and was once a farm supply store. Since its recent restoration, the inside is now reminiscent of a Spanish courtyard with red-tiled roofs, “Romeo and Juliet” balconies, and a dark blue ceiling adorned with stars. It’s a treasured gem in the heart of historic downtown.

7. Step Back In Time At The Winter Garden Heritage Museum

The Winter Garden Heritage Foundation started its efforts to preserve the architecture and heritage of West Orange County in 1994. The foundation operates two different historical museums — the Winter Garden Heritage Museum and the Central Florida Railroad Museum. The Heritage Museum sits inside the 1918 Atlantic Coast Line Depot. Inside you’ll tour displays, artifacts, and history from Winter Garden’s past as a part of the citrus industry. There are antique citrus labels and a citrus packing house replica, a nod to the town’s roots. A special kiosk shares details about the area’s fascinating history. Archeological finds include Native American pottery, beads, tools, arrowheads, and pioneer settlement history. Outside the museum, you can find an original 1943 Cheshire caboose, a 1950 firetruck, and farm equipment used in the citrus industry. These items are interactive, and visitors are encouraged to explore them.

Central Florida Railroad Museum (Photo Credit: Jeanine Consoli)

8. Explore Winter Garden’s Railroad Ties

The Central Florida Railroad Museum is operated by the Central Florida Railway Historical Society. Admission is free, and whether you love trains or history, it’s worth a visit to explore the significant past of Central Florida’s railway. The exhibits and photos are a marvel, including the collection of 25 different patterns of dining car China and silver service from America’s historic passenger trains. Suppose you travel with grandkids or just love a model railroad exhibit. In that case, you will appreciate the HO scale model railroad and the Thomas the Tank engine layout. You’ll find books, gifts, model trains, and original artwork for sale in the gift shop.

The old Winter Garden fire station, built in 1938, is now the home of the Winter Garden Arts Association and SOBO Art Gallery. The association and gallery reside in a historic building that remains in the hearts of older residents who still remember hearing the siren wailing at noon, signaling lunchtime for town residents. Along with presenting art exhibits, offering classes, and presenting local artists a place to receive awards and recognition, the mission of the WG Art Association is “to encourage individual creativity and artistic expression” and to expand public access to art. SOBO will reopen on April 7th, but public art is displayed around town.

entrance to Gatorland (Photo Credit: Jeanine Consoli)

Pro Tip 

Not far from Winter Garden, and only a short 20-minute drive, is Gatorland. Gatorland is a 110-acre wildlife preserve that is pure Florida kitsch. It’s a fun place to visit and takes about 3–4 hours to enjoy everything in the park. Alligators (including rare white leucistic alligators) and crocodiles, from hatchlings to 14-footers, are part of the attraction. There is also an aviary, a petting zoo, shows, and other exciting attractions like zip lines. Gatorland has been running since 1949 and is a premier wildlife attraction still privately owned by founder Owen Godwin’s family. A visit here offers a unique experience and an education about alligators, one of the most misunderstood reptiles on the planet.

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