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.
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 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...
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 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 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...
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,...
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 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...
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 north to Lake Alfred in central Florida. As its name implies, you'll pass numerous lakes...
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 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...
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 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. The western end 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...
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 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...
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...
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...
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 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...
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...
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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...
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 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...
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...
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 Chain of Lakes Trail stretches for more than 3 miles along a former railroad bed from downtown Winter Haven north to Lake Alfred in central Florida. As its name implies, you'll pass numerous lakes...
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 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 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 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 Good Neighbor Trail runs 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. The western end of 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...
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...
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...
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 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 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...
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,...
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...
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...
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 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 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 north to Lake Alfred in central Florida. As its name implies, you'll pass numerous lakes...
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 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...
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 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 Good Neighbor Trail runs 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. The western end of the...
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 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 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...
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...
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 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 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 trail could've been fun but it was flooded in the section where we tried to enter. Maybe we'll have better luck next time!
10-5 17,,,,,,Trail is closed at Polk City due to Hurricane Irma damage.Haven't checked the Green Pond or Mabel areas.
Great bike trail! Beautiful ride around lake in the town of Clermont. Nice challenge heading east with lots of rolling hills. Great work out and great scenery! Connects to West Orange Trail so you can ride for miles and miles. Fast or slow it is a very fun and enjoyable ride. One if the best around!
The trail is beautiful! Great for all types of riders. Family friendly to serious riders. Short or long rides the trail is the perfect place for exercise. I love the casual rides with my family. Also, love the long rides on my road bike for serious but fun workouts. Beautiful scenery to enjoy all throughout trail. One of the best bike trails in the region.
the view was far better then what i expected we parked at Cypress Point Park ended up being 11.02 from there but it also connects to other trails as well. its a must
I learned the trail is not patrolled by law enforcement making escape from an attack impossible. My bicycle was destroyed and I was severely beaten by two bearded bicycle riders I never encountered before. Can be a dangerous ride.
This trail delivers. It is remarkable to have a trail go over 10 miles with only 1 road intersection. surface is in above average condition. the trail is shaded most of the day, except midday when I was there. Turtles, hawks and other animals are a bonus.
Too short. Too ugly. Too bad, it could be better if it connected to something else.
I rated this as a 4 only because it connects to the Van Fleet trail. It in itself is nothing special but the fact that it connects makes the total length 35 miles. So if you're ready for Straight flat ride of 70 miles that is nice with about 40% shade this is a great ride. Bring lots of water. The trail end has awful water and it's a long way back to the water supply. The trailhead here is also safer than the Van Fleet trailhead in Polk city.
I ride this trail 3-5 times a wk. Starting at the north end: the N trailhead is next to a sheriffs office so it is a little safer. No RR or water there. 1 mile into ride there's acovered bridge. .5 Mi. to spur to a nature preserve (Circle B Bar) The spur is nice for wildlife. One can continue into the reserve with mt bike for terrain. I just ride the .5 spur and then back. After 2.5 miles total there is a trail head (highlands city). RR and water. Across street is Bike shop. The trail goes another 3 mi. to another spur. This one is 2 mi. Then 2 more mi. to Bartow, fl. To trail head Another covered bridge. After bridge is major highway with no easy way to cross and only 100 feet of trail on across hwy. I'd stop at bridge. Good ride. 3.5 stars!
I got a great workout on this trail but the many stop signs, crossing roads and yield signs took away any sense of relaxation, escape and enjoyment.
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