Explore the best rated trails in Winter Haven, FL. Whether you're looking for an easy walking trail or a bike trail like the Orlando Southeast Trail and Orlando Urban Trail. With more than 42 trails covering 378 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.
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 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 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...
This multiuse path skirts the south shore of East Lake Tohopekaliga (fondly known as East Lake Toho) in St. Cloud, Florida. The trail is paved, and stretches about 2 miles point-to-point, paralleling...
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 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...
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 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,...
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 Baldwin Trail is a 12-foot wide multi-use trail that circles Lake Baldwin in Orlando Florida. The asphalt trail is wide enough to accommodate different types of users, including older...
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 Old Fort King Trail is a 6.7-mile mixed-surface trail in west Central Florida. The trail consists of two parts: starting from John B. Sargeant Park, a 2.2 mile paved portion heads north, along 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,...
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 Hardy Trail is a mile long walk or ride in the heart of Dade City. The trail sits on a converted railbed, and travels south from Church Avenue. Residents love using the trail to run or jog or walk...
It should take about 50 minutes to walk the Tampa Riverwalk from end to end, but chances are, it'll take you much longer than that. Tampa's waterfront abounds with attractions for the whole family -...
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...
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...
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...
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 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...
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 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 Lake Baldwin Trail is a 12-foot wide multi-use trail that circles Lake Baldwin in Orlando Florida. The asphalt trail is wide enough to accommodate different types of users, including older...
This is a dedicated bike-ped sidepath along Pleasant Hill Road in Kissimmee, Florida. The north-south trail extends from Cypress Parkway to Orange Blossom Trail (US Highway 17/ 92) through a setting...
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, 20-mile route is...
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 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 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,...
This multiuse path skirts the south shore of East Lake Tohopekaliga (fondly known as East Lake Toho) in St. Cloud, Florida. The trail is paved, and stretches about 2 miles point-to-point, paralleling...
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...
Combining asphalt off-street paths and sections of sidewalk (particularly the eastern arc of the loop), the Kissimmee Loop provides access from the city’s residential neighborhoods to many amenities,...
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...
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 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...
It should take about 50 minutes to walk the Tampa Riverwalk from end to end, but chances are, it'll take you much longer than that. Tampa's waterfront abounds with attractions for the whole family -...
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 Neptune Road Recreational Pathway, also known as the Bill Johnston Memorial Pathway, connects Kissimmee's Lakefront Park to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee...
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...
The Neptune Road Recreational Pathway, also known as the Bill Johnston Memorial Pathway, connects Kissimmee's Lakefront Park to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee...
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 Old Fort King Trail is a 6.7-mile mixed-surface trail in west Central Florida. The trail consists of two parts: starting from John B. Sargeant Park, a 2.2 mile paved portion heads north, along the...
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The Town-n-Country Greenway is part of Tampa's network of trails and non-motorized greenways. You can access the paved trail from a parking lot on Webb Road, just south of Woodbridge Boulevard and on...
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,...
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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...
It should take about 50 minutes to walk the Tampa Riverwalk from end to end, but chances are, it'll take you much longer than that. Tampa's waterfront abounds with attractions for the whole family -...
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 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...
Combining asphalt off-street paths and sections of sidewalk (particularly the eastern arc of the loop), the Kissimmee Loop provides access from the city’s residential neighborhoods to many amenities,...
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, 20-mile route is...
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 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 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...
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 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,...
This is a dedicated bike-ped sidepath along Pleasant Hill Road in Kissimmee, Florida. The north-south trail extends from Cypress Parkway to Orange Blossom Trail (US Highway 17/ 92) through a setting...
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...
It’s right next to a major highway…what else do I have to tell you?
Walking it is better than taking a lot of time to unload a bike!
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.
It was such a beautiful ride but I couldn’t follow the bike path with street crossings and all. I wish I had an app that could serve as a guide…I loved the trail so I’ll do it again.
This was a relatively flat sidewalk run that circumnavigates the lake. I started on Golfview Drive and went left. From here, you have the lake on your right and constant traffic on the left. Fortunately, there was a burst of rain as I started my run in the mid afternoon when it was really warm. At about three miles I was hot and needed to cool down. With the shore so close to me, I was seemingly deterred from approaching the shore because there were "private property" signs posted at every boat dock along the way. Nevertheless, this did not stop me from cooling off at the third mile.
I approached the clear water and made sure there were no dinosaur-type creatures lurking below before sticking my hand in the water. After dousing myself with cool water, I was able to carry on again. I am not a road runner and the concrete was a challenge for me as I was running in my Nike Terra Kigers. I walk a few times but this was primarily due to the heat. I didn't bring any water to drink and no calories to ingest. I pushed on, though. At the half way point, the lake is well behind giant houses with lavish exteriors and sprawling yards. This portion was rather delightful to see.
I saw a few runners going in the opposite direction and I waved. They waved in return. At the six mile point, I steered myself to a small beach and again doused myself with water. This was refreshing. Then I cruised again on the concrete pathway. At mile eight, the houses disappeared and the lake returned. The wind pushed against me and the sun burned my face, but I kept running. Up ahead, a street sign said, "Golfview Drive at next light." Hopeful, I pushed on. I reached the finish line, but realized it was about 9.8 miles, so I kept going until I got 10 miles. Time 1:39.
These reviews are pretty dated. There are two sides of this trail separated by a bridge in the middle. The Clearwater and the Tampa side. The Clearwater side up to the bridge is nice and peaceful. Not a lot of pedestrians. There is a place along the beach to park on the Clearwater side, but it's expensive like $3 for one hour.
After the bridge, you're on the Tampa side. Here's where it goes downhill (no pun intended). It didn't used to be like this. I've lived here for 7 years.
When I first started riding on these trails, their wasn't too many people on them. They understood trail etiquette. You could get a good workout.
The Tampa side was always a little busier, but lately, it's gotten ridiculous. Tons of walkers and SLOW bikers who won't move over no matter how many times you call out. No trail etiquette. Kids play in the middle of the trail and their parents could care less. They let their kids run out in the middle of the trail no matter who is flying by.
Those two parts of the trail are only 7 or 8 miles long before you have to cross traffic. The park at the end on the Tampa side is dangerous if you're not paying attention. Cars do not watch out for pedestrians when turning into the park. In Tampa, in general, cars have NO respect for bike riders or pedestrians.
The trail continues on, but you have to cross a few dangerous intersections. You get to a concrete trail alongside the bay. It's hard to see around the corners, so you can't ride too fast. Again, not the best for road cyclists. It continues after the intersection that goes to the Hyatt. This last part of the trail is very bumpy. Not a smooth ride unless you have a cruiser or mountain bike.
If you're a serious road cyclist, I wouldn't bother coming here. It will be hard to get a good work out.
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.
The listed 3.7 miles is from the Hammock Park ranger station to the highway intersection. The shown map does not go all the way west. There is a $2 fee to continue west past the ranger station and into the park BUT the ride through it is outstanding. Not to be missed - be sure to stop at the Cypress Swamp trail and walk the boardwalk/catwalk over the swamp.
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.
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