Florida Travel / Winter Garden Florida
Winter Garden, Florida has preserved its historic charm while catering to foodies and outdoor lovers. ©Dawn Damico
While the rails that once carried the train down Plant Street have been replaced by brick-paved roads, it’s clear that Winter Garden, Florida has succeeded in masterfully honoring its past, embracing the present, and preserving its historic charm. If you’re like me, and enjoy picturesque small towns, then you will be delighted by a trip to Winter Garden. A surprising discovery just a short drive from Orlando’s bustling theme parks.
Established in 1903, Winter Garden’s roots stretch back to the 1850s when settlers of European descent were drawn to the fertile land along Lake Apopka. However, long before the land was parceled off with small settlements, the Timucua inhabited and farmed the area and later. the Seminoles.
Lake Apopka
Lake Apopka was once dubbed the “large-mouth bass capital” and the area surrounding its shores drew aspiring farmers from near and far. From the muck of an untamed land, early settlers planted citrus groves and rows of vegetable crops to take advantage of Florida’s eternal summer. As the name suggests, they created a winter garden that supplied produce year round to cities across the nation, and a town was born.
Historic Downtown Winter Garden
Many of the original wooden buildings burnt down many years ago and were replaced with brick buildings. This home with the purple cow is located next to the Plant Street Market. ©Dawn Damico
As you walk down Plant Street’s wide grassy median in the historic downtown district, you’re serenaded by music drifting through mature oak trees and lush greenery. You’ll likely start humming along to one of the “oldies but goodies.”
Lining the street are lovingly restored brick buildings that now house an eclectic mix of restaurants and boutiques that cater to visitors looking to escape the frenetic pace of Orlando’s theme parks, outdoor enthusiasts exploring the popular West Orange Trail, and locals that savor their town’s laid-back vibe. Towering above all of it is the water tower with Winter Garden painted on the side. It’s easy to enjoy the shade of a tree and slower pace of life, even if just for a moment.
Centennial Plaza
The heart of Winter Garden can be found at Centennial Plaza. You’ll find people swaying on porch-style swings in the shade of arbors where gnarled tree roots climb and purple flowers dangle. The calming sounds of the fountain decorated with tiles make this a perfect place to enjoy a morning cup of coffee.
Kids will enjoy the interactive splash pad lined with benches where parents look on as they play. Even on a hot Florida summer day, the town’s abundant shade and community gathering places offer a cool refuge.
Where to Eat in Winter Garden
An inviting greenspace in the shade is perfect for an afternoon picnic. The Interactive Splash Pad is directly above the steps for some kid-friendly play. ©Dawn Damico
With over 50 restaurants and bakeries serving everything from burgers, ceviche, and sushi, to wine, coffee, tea, and cocktails, Winter Garden is a food lover’s paradise.
While visiting on a Monday morning, some of the businesses and the museum were closed; however, the most restaurants were open.
Rosallie Le French Cafe is just one restaurant in historic downtown Winter Garden Florida to enjoy breakfast, brunch, or lunch. ©Dawn Damico
Rosallie Le French Cafe
I discovered a cozy spot that transported me to Europe with its charming ambiance. Breakfast at Rosallie Le French Cafe included their Rose Mocha, adorned with a tart, gummy, flower-petal-like garnish. Their brunch plate, served on a sleek black platter, felt like a personal charcuterie board with French Toast, poached eggs, bacon, and sliced meats.
They also serve sandwiches and wine, making it the perfect spot to put together a picnic to enjoy later in the day either along the West Orange Trail, nearby Newton Park by the lake, or Oakland Nature Preserve.
Plant Street Market has gone from ugly duckling apartment building to lively community space with a brewery, specialty food vendors, and more! ©Dawn Damico
For something a little livelier, head to the brick building next to the purple cow. With a cavernous industrial interior, I thought it was a transformed commercial packing house from yesteryear. I was wrong.
Plant Street Market is home to Crooked Can Brewing Company and a host of indoor vendors and specialty food stalls. Before that, it was an ugly apartment building in need of a little love. Enter Crooked Can Brewing Company, who breathed life into a neglected structure.
Their vision of creating a community gathering place, which happens to brew and serve great craft beer, turned that ugly duckling of a building into a must-visit Winter Garden destination.
You’ll find a 12,000-square-foot indoor space filled with industrial charm, anchored by the brewery, and lined with various permanent and rotating vendors. Step outside to an 8,000-square-foot patio area beneath the shade of massive oaks.
Crooked Can Brewing Company had a vision to create a community space and their 8,000 square foot patio invites visitors make memories here. ©Dawn Damico
What might you find at Plant Street Market? Handcrafted popsicles, artisan cheeses and a fresh-off-the-farm butcher. Add to that wood-fired pizza, gourmet donuts, freshly rolled sushi, oysters, empanadas, fresh-pressed juice, loose-leaf tea, and designer chocolates and you’ll want to take some home with you. If you’re traveling, consider bringing a cooler to carry some of your products home.
Not all vendors are open every day, so check their website. Saturdays can get pretty lively because of the nearby award-winning and world-famous (at least in Florida), Winter Garden Farmers Market. The gal at Crooked Can Brewing Company told me it’s a great place to be on the weekends.
Get Outside in Winter Garden
A wide meridian feels more like a park as you stroll down Plant Street in Winter Garden, Florida. ©Dawn Damico
Winter Garden caters to the active crowd with its pedestrian and bicycle-friendly layout. The West Orange Bike Trail goes right through the center of town and at some point it will be connected to the larger Florida Coast-to-Coast Trail. There’s a running store in town which is perfect if you are ready to run or walk the trail. Bike rentals are available at several locations along the trail so if you have the time and inclination to get a little wind in your hair, check them out!
Brick buildings, colorful awnings, and mature oaks bring back the vibe from yesteryear as the ecclectic mix of shops and restaurants cater to our modern preferences. ©Dawn Damico
In addition, nature lovers should visit the Oakland Nature Preserve or Newton Park mentioned previously.
Lake Apopka is an environmental cautionary tale that is steadily working its way towards a happy ending. Once flourishing with fish and wildlife, it has been recovering after more than 100 years of negative effects caused by agricultural runoff and levee construction. Planning and revitalization efforts began in the late 1990’s and today, some fishermen call this place a hidden treasure. A great source for the lake’s history, current conditions, and where to fish now is the Bass Online website.
Visiting Winter Garden Florida
Winter Garden proves that you don’t need to venture far from Orlando’s popular attractions to step back in time and experience Florida’s authentic charm. ©Dawn Damico
While my time in Winter Garden Florida was relatively brief, it definitely left me eager to return. I’m looking forward to exploring the Heritage Museum, which was closed during my Monday visit, experiencing the Saturday Farmers Market, sampling more of the culinary offerings, and riding the bike trail.
Winter Garden proves that you don’t need to venture far from Orlando’s popular attractions to step back in time and experience Florida’s authentic charm. This pretty little town is the perfect blend of history, culture, and small-town hospitality.
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