Find the top rated trails in Winter Haven, 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.
_138004_sc.jpg)
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...
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 Colonial Town Center (Fashion Square Mall)...
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...
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...
Opened in 2001, the Suncoast Trail is part of Florida's Statewide Greenways and Trails System. The trail parallels the Suncoast Parkway, beginning in northern Hillsborough County, and heads north...
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...
The Hammock Road Trail parallels its namesake from Highlands Hammock State Park to Lake Jackson, allowing Sebring residents easy access between two of the city's natural treasures. The state park...
The Flatwoods Park Trail is located within a park of the same name. Flatwoods Park is just one of five parks that make up the Wilderness Park system. These parks include Trout Creek, Dead River,...
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 Sebring Parkway Trail follows this major thoroughfare though downtown Sebring. Trail-goers will pass by three popular recreational attractionsSebring Lake, Dinner Lake and Lake Jacksonas they...
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 Lake Jackson Trail circles this popular swimming and boating spot in the heart of Sebring. Trail-goers will enjoy waterfront views along the lake's sandy shores and connections to other trails in...
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...
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...
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...
Opened in 2001, the Suncoast Trail is part of Florida's Statewide Greenways and Trails System. The trail parallels the Suncoast Parkway, beginning in northern Hillsborough County, and heads north...
The Hammock Road Trail parallels its namesake from Highlands Hammock State Park to Lake Jackson, allowing Sebring residents easy access between two of the city's natural treasures. The state park...
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...
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 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...
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 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,...
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 Flatwoods Park Trail is located within a park of the same name. Flatwoods Park is just one of five parks that make up the Wilderness Park system. These parks include Trout Creek, Dead River,...
The Courtney Campbell Trail provides pedestrian and bicycle access along the southern side of the Courtney Campbell Causeway, linking two communities, Tampa and Clearwater, and two counties,...
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...
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 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 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...
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...
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...
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 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 Courtney Campbell Trail provides pedestrian and bicycle access along the southern side of the Courtney Campbell Causeway, linking two communities, Tampa and Clearwater, and two counties,...
The Flatwoods Park Trail is located within a park of the same name. Flatwoods Park is just one of five parks that make up the Wilderness Park system. These parks include Trout Creek, Dead River,...
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 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 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...
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...
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...
Opened in 2001, the Suncoast Trail is part of Florida's Statewide Greenways and Trails System. The trail parallels the Suncoast Parkway, beginning in northern Hillsborough County, and heads north...
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 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...
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 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...
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...
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...
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 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.
If you are in to going fast than use the roads, this is for relaxing rides. Not sure why there are so many complaints, I find the trail quite relaxing and very nice. Not sure where people are riding saying they have to stop ever 1/4 mile. I've been riding this trail since it first opened. I remember walking down the railroad tracks that follow the same path when I was a teenager back in the early 70's.
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.
You can park at Veteran's Park. This trail is a nice 10 mile ride, however, I will say that it is definitely all sidewalk. If you are planning on riding your "road bike" ...don't !! If you do, you can ride in the road for part of it but the roads are very busy and then there is about 3 miles of the trail running along Hwy 27 which is very noisy & not enjoyable. Because of this, I took my bike with hybrid tires instead. No clip in pedals because there is too much stopping/starting. On Hwy 27, cars are wizzing past. Definitely no way to ride your road bike on roadway there. The sidewalks are at times, uneven and blocked with tree trimmings, etc....There are many driveways and cross streets to watch for. Pay close attention here for moving vehicles. I was able to follow the trail just fine around the lake but there are no markers to keep you on track. Just follow the lake. I made two rounds in about 1.5 hrs.
Road this trail with 2 other couples. Started at Gulf to Bay and road towards Tampa. Such a great experience. Very easy for all levels. Do not be frighten by the mid ride bridge, it was constructed to be a easy climb. Whiskey Joe's at the end is a nice reward. Only complaint, does anyone in this state say "on the left!" It is aways a surprise when you get passed. This is the same on ALL the trail we have walked or ridden in Florida in the last two months.
Put this on the bucket list, you won't be disappointed.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_138004_st.jpg)
_3446_st.jpg)
