Last updated on August 9th, 2026 at 07:47 pm
Thirty years ago, Winter Garden, a city 15 miles west of Orlando, had a faded, decaying downtown. Businesses had moved out; people and vitality had followed.
But then, area leaders made two things happen:
- The West Orange Trail, a 22-mile bicycle trail running right down the middle of the main street, opened in 1999.
- A $4.5 million project to beautify and preserve the historic downtown was completed a few years later.
Today downtown Winter Garden is a quaint old-fashioned neighborhood full of restaurants, museums, fountains, bike shops, boutiques and all sorts of people on bicycles and foot.
Winter Garden now makes a perfect weekend getaway for bicyclists and lovers of Old Florida. It is being touted as the best evidence around why Florida needs to build more bike trails and connect the ones already built.
Personally, I want everyone to go to Winter Garden to see what magic can happen when you combine bike trails with historic preservation. (Here’s a separate piece just on the highly recommended West Orange Trail.)
Winter Garden and Lake Apopka revived
While it’s gradually being swallowed by sprawling metro Orlando, Winter Garden is a historic town established in the 1890s with a heritage of citrus groves and railroads.
The Historic Edgewater Hotel, now closed for refurbishment, is at the center of downtown. It was built in 1924 to bring northern tourists to Winter Garden to fish in nearby Lake Apopka, which teemed with trophy-sized bass. In addition to the hotel, there were 20 fish camps on the lake in its glory days. The Edgewater Hotel closed in 2025 and new owners vow to refurbish and reopen it.
Lake Apopka is Florida’s third largest lake and had the unhappy distinction of becoming its most polluted in the 20th century. Years of abuse peaked in 1980 when a pesticide manufacturer nearby spilled toxic chemicals into the water, killing thousands of birds, alligators and other wildlife. (The spot became a Super-fund clean-up site.)
Today, clean-up efforts are working and Lake Apopka is making the same kind of comeback as Winter Garden. We picnicked along the city’s Tanner Park on Lake Apopka’s shore and saw osprey, heron, alligators and hawks all thriving around the blue waters of a lake no long a sludgy sick green.
Things to do in Winter Garden
1. Bicycle the West Orange Trail
The best reason to go to Winter Garden is to bicycle the West Orange Trail, for which we have a separate guide. It’s a great bike trail: Once a rail line, it is safely separated from traffic with a gentle grade. It’s smooth, wide, has excellent signage, a good amounts of shade and scenery and is long enough for even the most energetic bicyclists to get a work out. Read more here.
2. Stroll the attractive downtown
The next best thing to do in Winter Garden is stroll the attractive downtown. Benches, landscaping and fountains, including a large interactive one, make it an appealing place to relax. On Friday evenings, Winter Garden features live music in the downtown gazebo from 7 to 9 p.m.
3. Visit the Plant Street Market and Crooked Can Brewery
This lively food court in the walkable downtown is anchored by a craft brewery, Crook Can Brewery, which wins raves for its indoor and outdoor seating. You can get a wide variety of food, from mac and cheese to barbecue to empanadas to hand-crafted popsicles.
4. Browse a free local museum
In the downtown area, there are two history museums. Both are free, small and open every afternoon: The Central Florida Railway Museum , where railroad buffs will find a remarkable collection of railroad china and other items, and the Winter Garden Heritage Museum, which has an old fire truck, a tractor and caboose and exhibits on citrus and Lake Apopka, among others. In both, staff members are eager to show and talk about the local history.
Things to do near Winter Garden
5. Hike at Lake Louisa State Park
A half hour away from Winter Garden is Lake Louisa State Park, worth visiting for its rolling hills, cypress trees draped with Spanish moss, old citrus trees, gopher tortoises, wildlife and 20 miles of hiking trails. Here’s our story on Lake Louisa State Park.
6. Bike in rural solitude on the Van Fleet Trail
If you’re up for another rail-trail, consider the Van Fleet Trail in Polk City, which is about 45 miles west of Winter Garden. This trail offers 29 miles of rural solitude through the Green Swamp. Here’s a Florida Rambler story on the Van Fleet Trail.
Resources for planning a visit to Winter Garden
- West Orange Trail
- The Historic Edgewater Hotel (now closed)
- The Central Florida Railway Museum
- Winter Garden Heritage Museum
- Winter Garden Farmers Market, Saturdays, 9 a.m. to 2 p.m.
- Garden Theatre