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 Orlando Southeast Trail . With more than 50 trails covering 428 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 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 Orlando Southeast Trail is a collection of multiuse pathways crisscrossing Lake Nona, a master-planned community southeast of the City of Orlando. Narcoosee Road, running north-south, serves as...
This trail branches off from the Leesburg-Wildwood rail-trail and will some day reach Fruitland Park, about 3 miles away. The current paved portion extends 0.7 miles, cutting a shaded swath past...
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...
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 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 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 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 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 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 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...
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...
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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 startled with humble beginnings of just over 1 mile, beginning...
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 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...
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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 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...
With a final 3.5 miles paved in between Osteen and Farmton in 2021, the East Central Regional Rail Trail is complete. The trail extends more than 50 miles between DeBary and Edgewater with another...
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...
This short trail acts as a connector, delivering residents from their neighborhoods to the south shore of East Lake Tohopekaliga. The trail runs the length of a linear park that sits in the median...
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 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...
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...
This trail branches off from the Leesburg-Wildwood rail-trail and will some day reach Fruitland Park, about 3 miles away. The current paved portion extends 0.7 miles, cutting a shaded swath past...
Fountain Lake Trail is just short of a mile long, and occupies a former CSX railroad corridor. The trail is built to accommodate both pedestrians and cyclists, as well as other non-motorized users....
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...
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 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...
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...
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...
As its name suggests, the Leesburg-Wildwood Trail is planned to connect the two communities via an off-street, walking and biking pathway. Presently, the trail extends between Veech Road and N. 14th...
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 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,...
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...
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 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 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 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 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...
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...
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...
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 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...
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 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...
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 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 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 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 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;...
Located in Leesburg, Florida, this two-lane, asphalt trail parallels Canal Street, connecting to the Venetian Gardens Park at its southern end. The park is spread out over 45 acres tucked into the...
The Orlando Southeast Trail is a collection of multiuse pathways crisscrossing Lake Nona, a master-planned community southeast of the City of Orlando. Narcoosee Road, running north-south, serves as...
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 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...
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...
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 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...
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,...
Not really sure why the lack is signage on this trail has not yet been improved. Has the county not read the reviews mentioning signage issues? It’s not like it hasn’t been a issue very long. The trail is nice. I rode from the Minneola Trailhead to the Winter Garden Station today. There were no maps of the trail that I could find at Minneola. When heading to West Orange you come to what is sort of a fork in the trail at Hancock Road. There is signage at the intersection but no arrows or plain direction to West Orange. I first took a right on Hancock and followed that trail which clearly wasn’t correct because it takes you to the very busy area in of Highway 50. I back tracked to the fork in the road then went left. Correct way. Still poor signage. Please Orange County fix this issue.
I usually park off of markham roads road but honestly the trailer is really nice and a lot of nature. I really appreciate how smooth the asphalt is, no bumps or anything besides sometimes leaves (as to be expected). Pretty solid trail though, I’m trying to find more like it.
Mostly shaded. Fun ride early in the day otherwise too many people. Small inclines. Park at land bridge and you can go horseback riding too.
What a wonderful job was done to make this a very enjoyable ride. The nicest trail I have ridden so far. A must if you are in the area.
The trail is closed during the the work day Monday through Friday, at the South trailhead entrance. This would have been good information to know. Prior to riding my bicycle 7 miles to that trailhead, and just have to turn around.
I’m giving this trail four stars precisely because most of it is just a simple dirt trail through a pristine Florida natural habitat -- we were just biking between the trees through beautiful nature. However, we did the trail during a very dry time in March 2022 and with 1.75 inch tires, and it didn’t hurt that we started on the dirt road out of the state park and didn’t know any better. If the conditions are wet you’ll want to do the non-asphalt part on a mountain bike with knobby tires.
While traveling, my wife and I were Pleased to enjoy this entire trail. It features a shared space between a nature preserve and residential area. Trail head also includes a visitor center that was an enjoyable stop as well, learning about the environmental and cultural history of the area. The most exciting aspect was to learn that we were biking along a watershed that is the start of the Everglades.
Not much fun crossing busy streets. We turned around and went home halfway into the ride. Too much work.
Well paved and easy to skate on without fear of tripping.
Great for skating. Pavement was even and didn't have to worry about falling!
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