Find the top rated trails in Winter Garden, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
The Sanford Riverwalk Trail follows the shoreline of Lake Monroe in Sanford, FL, north of Orlando. The riverwalk extends from US 17-92 to Mellonville Avenue and is one of the most scenic paved trails...
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...
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 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...
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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...
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 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; at...
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...
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,...
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...
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 Good Neighbor Trail will some day run 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. The...
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 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...
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...
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...
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...
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 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...
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...
The Good Neighbor Trail will some day run 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. 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 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; at...
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...
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 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,...
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 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...
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...
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 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...
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...
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 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...
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...
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 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 Colonial Town Center (Fashion Square Mall)...
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...
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...
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 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...
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 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...
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...
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...
The 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; at...
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 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...
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...
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...
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...
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 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 Good Neighbor Trail will some day run 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. 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 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 trail offers a view of nature and wildlife at its best as you ride along the trail. you will need to be on the lookout for snakes and turtle crossing the trail. The trail is clean and well maintained.
Good shade well maintained but mileage is poorly marked. Boombah softball field is a good rest stop with rocking chairs, shade and clean restrooms. Walking is fine not much of bike path due to all the stops.
We parked at Thornby Park, Restrooms and water. There were several parking areas also nearby and all marked nicely. We headed east and weren't sure how far the trail went. Some maps I looked at showed all the way to Titusville. It actually ends 8 miles. Five miles in there is a great diner (recommended by another reviewer), Osteen's Diner is a great stop to take a break and grab a bite to eat. This is a beautiful 8 mile, tree shaded trail with lots to see. Head west and you're on the Spring to Spring trail for an additional 8 miles. We'll possibly do that trail another day.
Lake Monroe is around the corner from where we parked, beautiful view.
Not marked very well and lots of stopping for traffic lights
Been on many paved trails from PA to FL. This rates as one of the best. Great scenery and solitude, wildlife everywhere! There are stretches where you will see no other cyclists for miles, especially early in the morning. Make sure to bring a tire repair kit.
This trail was a great start to our vacation as it is flat and about 22 miles long. We enjoyed the whole thing which has about 750 ft. of elevation change. Best part is Winter Garden which is a beautiful town with a couple of fantastic bike shops and lots of places to eat. It is about 6 miles in from the western end of the trail. Also loved the West Orange Bikes and Rentals as they set us up with great bikes for the week.
Now let's not get too excited, we are talking about 900 ft of climbing over 32 miles but it is nice since most everything else is flat. Great trail, segregated the whole way, easy to ride. Goes through Clermont which has lots of places to eat, some right on the trail.
We also did the Hancock extension to get the total miles up and it has a terrific view. Highly recommend this trail.
We started at the Mabel end because we wanted to get water at Green Pond and Polk City. There is no water at Mabel. Lots of shade, lots of animals on the trail. We were surprised that the trail outside of the State Park were just as good for viewing.
We saw lots of gators especially from the three bridges 2.5 miles north of Green Pond. We saw at least 5 gopher tortoises, a pileated woodpecker, vultures and deer along the way. Trail is in great shape but bring enough food for the whole day. Well worth the trip.
I rode this trail today (3/19/2018) and it is so pleasant. I stopped in Brooksville and had an expresso and muffin at Mountaineer Coffee. What a nice downtown square. Parked at the train depot museum with great bathroom facilities. The trail runs further than the map reflects today. The trail runs all the way east on Richbarn Road to the Croom WMA. I hear that this trail will be a part of the east west connector. So very pleased with the ride. I will watch for the extension into Croom WMA and return. After the ride I drove down to Dade City for good country cooking at Steph's Southern Soul Restaurant.
Just a caution that much of this trail goes, or will go, thru areas popular with hunters, in season.
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