Explore the best rated trails in Winter Garden, FL. Whether you're looking for an easy walking trail or a bike trail like the Cross Volusia Trail and Seminole Wekiva Trail. With more than 43 trails covering 400 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
The Lake Wales Trailway is a 2.3 mile, 12-foot wide asphalt path that circles most of Lake Wales. The trail serves both as a recreational and transportation asset, thanks to its proximity to a number...
This is a dedicated bike-ped sidepath along Pleasant Hill Road in Kissimmee, Florida. The north-south trail extends from Cypress Parkway to Orange Blossom Trail (US Highway 17/ 92) through a setting...
The Lake Baldwin Trail is a 12-foot wide multi-use trail that circles Lake Baldwin in Orlando Florida. The asphalt trail is wide enough to accommodate different types of users, including older...
Opened in 2017, Orange County's Pine Hills Trail spans 1.75 miles from Alhambra Drive to Silver Star Road in a western subdivision of Orlando. In the middle of the north-south route, a spur heads...
The Goldsboro Trail is approximately a mile long, located in the Goldsboro neighborhood of Sanford, Florida. The neighborhood was one of Florida's first incorporated Black communities but was annexed...
The Hardy Trail is a mile long walk or ride in the heart of Dade City. The trail sits on a converted railbed, and travels south from Church Avenue. Residents love using the trail to run or jog or walk...
The Hancock Trail is 6.5 miles of smooth as ice, undulating multi-purpose trail in Lake County, Florida. It’s wide - a good 14 ft - and the hilly topography can either be a moderate challenge or a...
About 20 miles west of Orlando, the South Lake Trail (also known as Lake Minneola Scenic Trail) takes in some of central Florida's most spectacular prospects. Nowhere in this region will you find more...
If you're traveling to central Florida, you won't want to miss the Spring to Spring Trail, which connects a number of small, friendly towns between Orlando and Daytona Beach, as well as many of the...
Neighbors in Avalon Park will appreciate this short local trail - a place to walk, bike and meet that's right on their doorstep. The trail runs just short of a mile east from the trailhead on Mailer...
The General James A. Van Fleet State Trail runs 29 miles through some of Florida's most scenic rural landscape. If you are looking to immerse yourself in wetlands and wildlife, it will not disappoint;...
The 46-mile Withlacoochee State Trail is a must-do pure Florida experience for any trail enthusiast. Situated between Orlando and Tampa, it hosts a steady stream of visitors and locals on its paved...
Note: Per a Florida Department of Transportation press release, "The Fort Fraser Trail will be closed at the Banana Creek Bridge from April through fall 2016 due to construction. The remainder of the...
The Chain of Lakes Trail stretches for more than 3 miles along a former railroad bed from downtown Winter Haven to north of Lake Alfred in central Florida. As its name implies, you'll pass numerous...
The Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Coy Drive in Orlando, just past the Fashion...
The Wilson Parkway Trail parallels the road of the same name, stretching north from Cherry Rd to its endpoint on Libby Rd. #3. It’s mostly a green ride, there’s not much variation in scenery. The...
This is a paved multipurpose trail connecting two cities in central Florida. The pathway stretches 3 miles from W Main St. in Tavares, parallel to US-441 S, and terminates just after Kinne Pearce Rd....
Bike, walk or jog along a safe separated multiuse path along State Route 415 between Osteen and Sanford. Points of interest include the East Central Regional Rail Trail (at the SR 415 trail’s northern...
Kewannee Trail is a charming, neighborhood trail in Maitland, Florida. More than just a recreation path, the trail is popular as a connective line from the neighborhood to several destinations...
When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...
The 46-mile Withlacoochee State Trail is a must-do pure Florida experience for any trail enthusiast. Situated between Orlando and Tampa, it hosts a steady stream of visitors and locals on its paved...
The Titusville Multi-Use Trail, also known as the Wuesthoff Trail, is a short and pleasant paved path located in the southern outskirts of the city of Titusville. The trail runs through Wuesthoff Park...
The General James A. Van Fleet State Trail runs 29 miles through some of Florida's most scenic rural landscape. If you are looking to immerse yourself in wetlands and wildlife, it will not disappoint;...
A rail-trail that's a bit wild and off the beaten path, the Flagler Trail runs for around fourteen miles through rural Seminole County, to the northwest of Orlando. Nearly the entirety of the trail is...
The Goldsboro Trail is approximately a mile long, located in the Goldsboro neighborhood of Sanford, Florida. The neighborhood was one of Florida's first incorporated Black communities but was annexed...
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The Marjorie Harris Carr Cross-Florida Greenway is on a mission to create a non-motorized conduit stretching 110 miles from the Gulf of Mexico to St. John’s River in Palatka. The corridor showcases...
The Wilson Parkway Trail parallels the road of the same name, stretching north from Cherry Rd to its endpoint on Libby Rd. #3. It’s mostly a green ride, there’s not much variation in scenery. The...
The Cross Volusia Trail will one day link the east and west sides of Volusia County, stretching 20 miles from Lake Beresford to the coastal city of New Smyrna Beach. Currently, it runs through the...
This is a dedicated bike-ped sidepath along Pleasant Hill Road in Kissimmee, Florida. The north-south trail extends from Cypress Parkway to Orange Blossom Trail (US Highway 17/ 92) through a setting...
The Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Coy Drive in Orlando, just past the Fashion...
The Old Fort King Trail is a 6.7-mile mixed-surface trail in west Central Florida. The trail consists of two parts: starting from John B. Sargeant Park, a 2.2 mile paved portion heads north, along the...
Kewannee Trail is a charming, neighborhood trail in Maitland, Florida. More than just a recreation path, the trail is popular as a connective line from the neighborhood to several destinations...
The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. The trail offers riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a...
The Lake Apopka Loop Trail is nearly 15-miles. There’s an abundance of nature as well as some background history regarding the lake. Spanning across former farmland along the north shore, Florida’s...
Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte Springs. This popular, well-marked, 14-mile route is...
Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping. The first segment...
The Good Neighbor Trail runs for just over 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. The...
Gertrude’s Walk spans three city blocks in downtown Orlando, providing access to offices and the city’s sports arena not far from its southern end. The trail runs adjacent to an active CSX and Amtrak...
When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...
In northern Orlando, the Gaston Edwards Trail provides a pleasant jaunt of nearly a mile along Lake Ivanhoe's eastern shore. (Hence, the trail is also known as the Lake Ivanhoe Trail.) The paved route...
This is a paved multipurpose trail connecting two cities in central Florida. The pathway stretches 3 miles from W Main St. in Tavares, parallel to US-441 S, and terminates just after Kinne Pearce Rd....
The Goldsboro Trail is approximately a mile long, located in the Goldsboro neighborhood of Sanford, Florida. The neighborhood was one of Florida's first incorporated Black communities but was annexed...
The General James A. Van Fleet State Trail runs 29 miles through some of Florida's most scenic rural landscape. If you are looking to immerse yourself in wetlands and wildlife, it will not disappoint;...
Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping. The first segment...
A rail-trail that's a bit wild and off the beaten path, the Flagler Trail runs for around fourteen miles through rural Seminole County, to the northwest of Orlando. Nearly the entirety of the trail is...
The Hardy Trail is a mile long walk or ride in the heart of Dade City. The trail sits on a converted railbed, and travels south from Church Avenue. Residents love using the trail to run or jog or walk...
Gertrude’s Walk spans three city blocks in downtown Orlando, providing access to offices and the city’s sports arena not far from its southern end. The trail runs adjacent to an active CSX and Amtrak...
Note: Per a Florida Department of Transportation press release, "The Fort Fraser Trail will be closed at the Banana Creek Bridge from April through fall 2016 due to construction. The remainder of the...
The Cross Volusia Trail will one day link the east and west sides of Volusia County, stretching 20 miles from Lake Beresford to the coastal city of New Smyrna Beach. Currently, it runs through the...
When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...
Connecting small communities and suburban neighborhoods, the 22-mile West Orange Trail is one of Florida's most popular rail-trails, thanks to its reputation and proximity to metro Orlando. Fifteen...
The Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Coy Drive in Orlando, just past the Fashion...
About 20 miles west of Orlando, the South Lake Trail (also known as Lake Minneola Scenic Trail) takes in some of central Florida's most spectacular prospects. Nowhere in this region will you find more...
Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the Cross Seminole Trail provides crucial residential links in this...
This is a dedicated bike-ped sidepath along Pleasant Hill Road in Kissimmee, Florida. The north-south trail extends from Cypress Parkway to Orange Blossom Trail (US Highway 17/ 92) through a setting...
Bike, walk or jog along a safe separated multiuse path along State Route 415 between Osteen and Sanford. Points of interest include the East Central Regional Rail Trail (at the SR 415 trail’s northern...
The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. The trail offers riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a...
The Titusville Multi-Use Trail, also known as the Wuesthoff Trail, is a short and pleasant paved path located in the southern outskirts of the city of Titusville. The trail runs through Wuesthoff Park...
The Chain of Lakes Trail stretches for more than 3 miles along a former railroad bed from downtown Winter Haven to north of Lake Alfred in central Florida. As its name implies, you'll pass numerous...
Combining asphalt off-street paths and sections of sidewalk (particularly the eastern arc of the loop), the Kissimmee Loop provides access from the city’s residential neighborhoods to many amenities,...
The entire trail is terrific but if you only want to do part of it, I suggest the bottom half. The other day we drove to Floral City Park and accessed the trail about a quarter mile down the road to the east. We began riding south on mostly uninterrupted and canopied trail. Along Istachatta Rd with beautiful fields and ranches. We connected with the Good Neighbor Trail at about mile 10 from the terminus and rode southwest. It’s a newer straight trail to Brooksville. We saw two other riders and nothing but trees. Turned around at the end and returned to Floral City. A beautiful 40 mile ride.
We started at the golf club. We only rode this trail for a very short distance - but what we did see the trail was absolutely beautiful. It was too challenging for my wife and I - we are in our mid 70s. Glad we gave it a shot. (Wish we were 10 years younger!
This is a beautiful ride through forest vistas and rolling hills. The asphalt is smooth like velvet. When you separate from the few trailheads, you can feel pretty lonely. We ride road bikes so the paved trail is not accessible from the Ross Prairie trailhead. There is accessibility to the west end of the trail about a quarter mile up SR-200 but no real place to park. We had to drive 8 miles to the 49th St trailhead to find a formal parking area. But, it was all worth it. Only two cross streets on the entire trail. It tunnels under some and a land bridge over I-75. We will return frequently.
Trail is in great shape.. nice view as you ride.. It is very short 8.5 mile round trip..
Trail is average.. no much to see.. 90% of the trail is next to a busy road... Trail is not road bike friendly... ok if you have mountain bike.. I will not recommend!!
Great for biking, skating, running, walking you name it. Nice wide paved path so there’s room for everybody. Scenic ride along the water with fun spots over and under bridges. Lots of benches and water fountains to stop at along the way.
Cycled the full trail North & South today for the first time:
Trail is extremely well maintained, with mileage markers, and water & restrooms at terminus points. Incredibly scenic. Tons of wildlife! Mostly shaded. Very courteous visitors when passing in both directions, and from behind.
Here's my main concern: Deer.
I was riding early on a Sat morning, on the trail from about 8:30 A.M. to 11:00 A.M.
I had TWO very close calls of deer leaping out of the forest, crossing directly in front of me. First incident was two deer about 40 yards ahead. They crossed, then two more turned around just as I passed the point of the first crossing. Second encounter was only about 10 feet in front of me! A true Yikes! moment. Had no time to react whatsoever, a large deer bounded out and across the trail. Luckily we didn't collide. I was riding about 18 mph, not overly fast (or slow). I'm curious if other cyclists have had similar encounters. Crashing hard on the trail would potentially be serious, since help may not arrive rapidly. Also passed about 10-12 other deer just off the trail. I'm wondering if there was some kind of herd movement today that explained so many deer sightings/encounters inside one single ride. Any additional experiences would be helpful, as I surely want to continue riding this otherwise wonderful cycling heaven trail.
I truly enjoyed myself. I rented a bike from West Orange Trail bikes & blades...amazing customer service by the way, and took off to the trails. I saw so many beautiful surprises; peacock ¿, a snake slithering pass my bike ¿, etc. the trail had walkers, joggers, rollerbladers, and so much more. Heavenly covered with trees if you’re not too big on direct sunlight. I love my experience every time I go¿
We rode from the withlAchoochee state trail to the opposite side in brooksville. Great ride, we packed a squeeze bottle with electrolytes in water and I have the camelbak mule 3L of water. I thought that would be sufficient to ride there and back. We also had 4 miles to go at the start and finish as we put in at the trailhead just north of 50. In total 28 miles. The brooksville end is supposedly in a place that isn’t the best part of town but having the bathrooms and shops near was a real pleasur. If you do this ride, it is absolutely necessary to have plenty of water as there isn’t a drop available for 19
Road the trail today. 11 miles into the trail as you cross maytown road the trail is under water. Prevented me from getting to maytown spur. Beautiful ride. Sun and shade.
I come here every morning to run and rollerblade and it’s amazing. Although, it’s not long it is very good pavement to rollerblade!
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