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.
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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;...
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...
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...
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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...
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...
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 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...
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...
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 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 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...
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...
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...
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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 nearly mile-wide...
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 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 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 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,...
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...
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....
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 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 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,...
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...
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...
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...
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...
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 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 nearly mile-wide...
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...
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 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...
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...
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 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...
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...
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 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...
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,...
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...
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...
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...
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...
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 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...
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 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,...
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...
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 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...
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 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 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...
I really like this trail. It is shady most of the way. It crosses a few small roads in the beginning. The rest of the way it tunnels under roads and there is bridge that goes over I-75. There are mirrors at turns so you can see if anyone is coming. Clearly marked signs and crosswalk where other trails crossover. The entire trail is 15.66 miles and ends at 200 for now. There are plans to extend it to Dunnellon. Theres a Walmart a mile and a half from the end. I the scenery is beautiful and there were a couple of people out riding horses. Overall I felt very safe on this trail.
Rode from Green Pond trailhead and except for a few rain showers it was a great ride.
Let's clarify - the name is a misnomer, it is not a loop. It is out and back on same path. Plentiful gators, up close and personal. We planned to stop at covered picnic area to find it populated by a few 4 footers. Fortunately, they scattered as we approached on our bikes. Needless to say, we sat atop the table back to bak to ensure a 360 view. Much larger gators in water and crossing path.
Love that there are long stretches to allow you to gain speed or cruise and take in scenery. We spotted an owl, soft side turtle, cougar prints and more.
Nice place to get out int he wilderness without travelling far.
The trail now runs the 10 miles from Brooksville to the Withlacoochie. Paving is complete but not officially open. Rode on Sunday but were not allowed when workers present, today. Expect that will end soon. Inaugural Ride set for Oct 14, an event following the annual Withlacoochie ride on Oct. 7
We used Inverness as our start/finish since the parking is perfect and we love the town of Inverness. The trail is well maintained with a good blend of sun and shade. Well marked and a good feel of “Old Florida”.
Been riding this trail for over 15 years and it's been a very good place to ride until about a month ago(06/2018 when everything change.The weeds along the trail haven't been cut,the trail has weeds growing in the cracks,the trash cans are always full of trash,and the bathrooms are a mess,no toilet paper,trash on the floors,toilets plugup.The bridge near the Polk City trailhead has been under construction for over a month.Maybe they should bring back Ross.He got the job done.
We are new to riding in Florida, and after searching Trailink, I found that this awesome trail was only a few miles from our place. We decided to park in Osteen and take the south end of the trail, before crossing over the bridge over 415. The trail is well maintained with bathrooms located in all of the parks which the trail rolls through. Our overall experience was a wonderful experience. Meeting a few turtles, road runners and yes, some really nice humans too along the way was pretty cool. The aqua colored Sulphur spring was incredible to see as it seemed to actually glow. When we rolled into Gemini Springs, it was amazing to see the large fish swimming below us in the crystal clear waters. The final destination was the added trail around Lake Monroe, which had it's share of sunlight, and but also had much more of Gods Balconies to shield us from the sun. Because of the weather, we had to cut our ride short on day one as we barely got back to our car before the storm hit. Day 2 was a perfect day with loads of sunshine, so we started at the northern end with plans to cover what we hadn't seen on day one, but ended up riding the entire trail once we got rolling. Thanks to all responsible for this wonderful trail.
I visited this Bike Trail for the first time yesterday AFTER our typical afternoon rain showers. Luckily for me Sun came back out, Trail was nice and cool. The views from the trail and the lake are AMAZING! Great Leg Workout too. Little hills in Florida - who knew?!?!? LOL
WOW I can not say enough about this trail. We rode all 29 miles of it from end point to end point for 60 miles total. The trail is totally flat. No incline at all. The trail wisp through marsh lands, Wooded land, Pasture fields and small towns at each end point trail head. There is plenty of shaded areas however the areas in the sun can get quite hot for long stretches. Lots of water is required for this ride. Along the way we say 6 10 to 12 foot alligators one 4 footer and numerous baby's about 1 to 2 feet long. We saw them from one of the many swamp overpasses. We saw none on the path or near it. The ones we saw were close to us but below us. We saw numerous turtles, pelicans, cows,panther,numerous style birds. The trail is about a 50 minute drive from Clearwater and we did that in rush hour. There were nominal places to eat or water fountains in comparison to typical trails. The trail is maintained well. There are sheltered areas to cool off about every 5 miles. The trail was also pretty well traveled the day we were on it. Still it was a pleasant ride. This is a great trail and I rank it 5 stars. I have traveled across the country on great trails. This is in my top five. Just be prepared for the unexpected and bring water. Limited food too.
We packed lunch and headed-out to the Osteen Community Center on Hwy 415. Parking and restrooms are excellent. We went west over the pedestrian/bicycle bridge and rode approx 6 miles to Green Springs. Easy ride with about half of the trail covered by a canopy of tree limbs. We visited the Springs and then had lunch at a park bench by the boat ramp over-looking Lake Monroe. We then rode the 6-miles back. A very easy-going enjoyable 12-mile ride. I will return to do the complete ride on the east section of Osteen and then turning back west and ride past Green Springs on the one-way 12-mile ride at a higher rate of speed. Must be a great kept secret as there were only a few people out on a Saturday!
Thank you for the trail.
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.
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