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 39 trails covering 385 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 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...
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...
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 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 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...
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...
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...
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After 30 years of planning, the first segment of the Shingle Creek Regional Trail opened in Kissimmee in November 2016. The paved trail spans just over 1 mile, beginning near Steffee Landing, south of...
Neptune Road RecreationalPathway connects Kissimmee Lakefront to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee Lakefront Park and runs along the north side of Lakeshore...
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...
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...
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...
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...
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...
The Auburndale TECO Trail connects Lake Myrtle in Auburndale with Polk City, where it meets up with the General James A. Van Fleet Trail. The Auburndale TECO Trail is flat and invites walkers,...
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...
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;...
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...
Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's northern neighborhoods. It winds by several lakes,...
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...
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,...
Neptune Road RecreationalPathway connects Kissimmee Lakefront to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee Lakefront Park and runs along the north side of Lakeshore...
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...
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 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...
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...
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...
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 Little Econ Greenway trail is just one section of the Orlando area's many fine trails. features riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a canal...
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...
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...
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...
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...
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...
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...
After 30 years of planning, the first segment of the Shingle Creek Regional Trail opened in Kissimmee in November 2016. The paved trail spans just over 1 mile, beginning near Steffee Landing, south of...
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...
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...
The Auburndale TECO Trail connects Lake Myrtle in Auburndale with Polk City, where it meets up with the General James A. Van Fleet Trail. The Auburndale TECO Trail is flat and invites walkers,...
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 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...
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...
After 30 years of planning, the first segment of the Shingle Creek Regional Trail opened in Kissimmee in November 2016. The paved trail spans just over 1 mile, beginning near Steffee Landing, south of...
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 US 92 Trail travels across northern DeLand, closely following the north side of the highway known locally as International Speedway Boulevard because it passes the famous racetrack at Daytona...
The Lake Underhill Path is a greenway linking four parks in Orlando near the Orlando Executive Airport in downtown Orlando. Work out stations dot the length of the trail, which is why you might hear...
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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 Little Econ Greenway trail is just one section of the Orlando area's many fine trails. features riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a canal...
Neptune Road RecreationalPathway connects Kissimmee Lakefront to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee Lakefront Park and runs along the north side of Lakeshore...
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...
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 Auburndale TECO Trail connects Lake Myrtle in Auburndale with Polk City, where it meets up with the General James A. Van Fleet Trail. The Auburndale TECO Trail is flat and invites walkers,...
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;...
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 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...
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...
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...
Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's northern neighborhoods. It winds by several lakes,...
It’s a nice area around the lake but not a nature trail at all.
Good area for some training runs. Only good hill section is the bridge over the turnpike. Some sections of the paved route are being pushed up by tree roots so be careful if doing any night running. Also street crossings across Neptune Road can be a bit adventurous and time consuming. Not all the street crossing buttons work. No parking at the end of the route in Saint Cloud but I park at Partin Triangle Park and then jump on the trail since I live on the Saint Cloud side.
I rode parts of this trail I hadn't been on before namely Edgewater to the split. Finding the parking area was easy but getting on the right trail wasn't. After you cross busy Park Ave you go on a narrow sidewalk and then take a right turn. At that point a wide paved trail (apparently a city trail) lies straight ahead with no marking, so I took the logical path and eventually wound up dead ended in front of a high school. To get back to the trail from where I was at I had to take a very busy, no shoulder road (Old Mission) to connect to the East Central Trail. On the way back, the ECT dead ended with no signs or arrows. Whoever manages this trail needs to install signs or at least arrows. Also, as far as signs go it would be nice to get some idea of point-to-point distances. For markings and signage this trail gets a BIG RED "F".
And while they're at it why not put in some porta-potties and water fountains--there are NO facilities or stores on this trail--so pack in your water & food supply.
With that said this trail was very nice & smooth with lush vegetation on both sides. Why not add to what's been done to make it more user friendly.
This is a great trail. Like the curves and gentle hills. The scenery is perfect. Makes for a perfect 30+ mile ride.
Nice trail has some elevation and not on road as may appear on map. Has some urban aspects plenty of room a few cross roads. Would be good if they added some longer spur trails.
2019.11.29 Black Friday, yep! Busy Shopping Centers & traffic...nope, NOT for this guy. I took my bicycle with me on an easy 20 minute urban train ride, from downtown Orlando to this BEAUTIFUL PARK in Kissimmee! The SunRail station is a short distance from Kissimmee Lakefront Park. FYI ...SunRail only operates during the weekdays. Ample Parking, Great for Bike rides, walks, jogging. I will return and explore the ride along side Neptune road
The Marjorie Harris Carr Cross Florida Greenway is the epitome of what a bike trail should be.The asphalt blacktop looks newly paved and is almost perfectly smooth the entire 15+ mile ride. It is plenty wide for two way traffic and passing with lots of nice curves and some hills passing through some truly beautiful woodlands in Central Florida just outside of Ocala. Wildlife abounds along its entire length. An added bonus is the 100's of miles of mountain bike trails that intersect along its length in many places. It is super well maintained and marked throughout on the pavement for any emergency that may need reporting. There are only a couple of road crossings with the majority being underpasses and a very unique overpass over Interstate 75. Anywhere there is a blind corner there are large round cornering mirrors and signs to notify you to slow appropriately. There are water and toilet facilities at the Santos Trailhead and further down their is an equestrian campground that also has accessible facilities. If you plan for a down and back ride it is a great workout and make sure to bring some hydration. A large part of the ride is shaded but there is enough sun exposure to warrant sunscreen. All and all, this is a top teir bike trail and worth the drive to get there if you have to travel. Truly My New Favorite Bike Trail! Highly Recommended!!!
Beautiful scenery but ride is very rough, part of the trail is concrete that’s coming apart.
My wife and I started at the Lake Monroe park and boat launch. Rode this portion north and east around the lake and then picked up the west end of the East Central Regional trail. I'm guessing about 32 miles round trip. Definitely a 5+ rating. The scenery and wildlife was amazing. We saw 2 bald eagles and a family of deer along the way. Visited Gemini Springs and Green Springs too. Also, at every street crossing we came to, all the motorists were so considerate. Evidence of a community that embraces the trails and the folks who use it. After our ride we drove to Central 28 brewing for a beer. We could have rode our bikes there but it was getting dark. Their beers are really good and they had a great food truck that night. For those that read this review I'll give you a tip. If you ride your bike to the brewery on a Sunday they will give you a beer for free !!
Awesome bike ride for those who don't need paved trails. There is nature galore with many species of birds and alligators everywhere. If you go down all the various paths you can easily exceed 30 miles of riding. The paths are from decently smooth to very rough. Recommended that you have a bike with suspension for your own comfort. A regular bike could make it of course but many areas with a very rough ride. There is a bathroom and water fountain at the trailhead but only porta potties in a couple of other places. Cars are alowed in certain parts from Friday to Sunday but shouldn't be a real issue for bikers.
Trail is very well maintained, rest areas plentiful along the way. Nice scenery
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