Find the top rated walking trails in Winston, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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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...
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 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...
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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...
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 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,...
Although short, the Bayshore Trail provides an important connection between two popular trails on Florida's west coast: the Courtney Campbell Trail and the Ream Wilson Trail. The paved north-south...
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 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 Tangerine Greenway follows a former trolley line that once ran between St. Petersburg and Gulfport on Florida's west coast. The paved pathway begins at Gulfport's Tomlinson Park and heads east in...
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...
Pinellas County has embarked on the impressive task of creating a 75-mile chain of trails, to be known as the Pinellas Trail Loop. When complete, Duke Energy Trail will be a 22.5 mile link in that...
The paved trail in Jay B. Starkey Wilderness Park stretches across the preserve for about 6 miles. Well-spaced shelters along the trail offer pleasant places to rest in the shade; many are even...
The North Bay Trail begins in downtown St. Petersburg with an easy connection to the scenic 42-mile Pinellas Trail at Bay Shore Drive SE. From there, the trail heads north along Tampa Bay, offering...
The Sebring Parkway Trail follows this major thoroughfare though downtown Sebring. Trail-goers will pass by three popular recreational attractions—Sebring Lake, Dinner Lake and Lake Jackson—as they...
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,...
The Marine Parkway Multi-use Path was constructed as part of a wider trail networking improvement effort in the city of New Port Richey. The ultimate vision is to have a continuous bike-ped connection...
The Ream Wilson Clearwater Trail will one day stretch across Florida from Tampa Bay to the Gulf of Mexico. Four miles on its eastern end are now complete and run through Safety Harbor. It will one day...
Widely regarded as Tampa Bay's best urban trail, the Upper Tampa Bay Trail provides a scenic escape from its congested surroundings. The original section winds through suburban Citrus Park on an...
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 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 paved trail in Jay B. Starkey Wilderness Park stretches across the preserve for about 6 miles. Well-spaced shelters along the trail offer pleasant places to rest in the shade; many are even...
The Sebring Parkway Trail follows this major thoroughfare though downtown Sebring. Trail-goers will pass by three popular recreational attractions—Sebring Lake, Dinner Lake and Lake Jackson—as they...
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 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...
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...
Widely regarded as Tampa Bay's best urban trail, the Upper Tampa Bay Trail provides a scenic escape from its congested surroundings. The original section winds through suburban Citrus Park on an...
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 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 Tangerine Greenway follows a former trolley line that once ran between St. Petersburg and Gulfport on Florida's west coast. The paved pathway begins at Gulfport's Tomlinson Park and heads east in...
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...
One of Florida's most popular and unique urban pathways, the Pinellas Trail stretches from St. Petersburg north to Tarpon Springs, and on into Pasco County with the opening of a 5-mile section in July...
The Ream Wilson Clearwater Trail will one day stretch across Florida from Tampa Bay to the Gulf of Mexico. Four miles on its eastern end are now complete and run through Safety Harbor. It will one day...
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 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...
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...
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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...
Although short, the Bayshore Trail provides an important connection between two popular trails on Florida's west coast: the Courtney Campbell Trail and the Ream Wilson Trail. The paved north-south...
Although short, the Bayshore Trail provides an important connection between two popular trails on Florida's west coast: the Courtney Campbell Trail and the Ream Wilson Trail. The paved north-south...
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;...
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 Ream Wilson Clearwater Trail will one day stretch across Florida from Tampa Bay to the Gulf of Mexico. Four miles on its eastern end are now complete and run through Safety Harbor. It will one day...
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 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...
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...
Pinellas County has embarked on the impressive task of creating a 75-mile chain of trails, to be known as the Pinellas Trail Loop. When complete, Duke Energy Trail will be a 22.5 mile link in that...
One of Florida's most popular and unique urban pathways, the Pinellas Trail stretches from St. Petersburg north to Tarpon Springs, and on into Pasco County with the opening of a 5-mile section in July...
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 Sebring Parkway Trail follows this major thoroughfare though downtown Sebring. Trail-goers will pass by three popular recreational attractions—Sebring Lake, Dinner Lake and Lake Jackson—as they...
Widely regarded as Tampa Bay's best urban trail, the Upper Tampa Bay Trail provides a scenic escape from its congested surroundings. The original section winds through suburban Citrus Park on an...
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,...
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 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 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 Marine Parkway Multi-use Path was constructed as part of a wider trail networking improvement effort in the city of New Port Richey. The ultimate vision is to have a continuous bike-ped connection...
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...
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...
They have opened the section that joins the two pieces shown on the map. Thus one can join the trail at the Tapestry development off Dyer Blvd and go all the way to Kissimmee Lakefront or to Pioneer Village. Great addition. Looking forward to them finishing off the northern section up to Osceola Parkway next as they acquired the easement rights in 2018.
Nice trail! North of Tarpon Springs is a bit boring, but the entire trail is very well maintained!
This beautiful trail has 4 parking lots @ the 0-10-20-29-mile markers. On 1Jan, Tom and I rode from Mile 0 @ the Polk city parking lot to Mile-15 out and back. We saw several box turtles and a few Gators in the water! On 2Jan we parked @ the Mile-20 Parking lot. Rode out and back to the 29-mile marker, then back to the 15-mile mark out and back! We saw quite a few more box turtles sitting out front of their burrows; if I parked bike and tried to get close for pic, they would quickly scurry back into the burrow! We enjoyed watching one cross as fast as she could from the opposite side of the trail back to her burrow... Saw a gator happily sunning self on side of trail! This trail rides primarily alongside a swamp on both sides... it is awesome if you like a natural setting with only 3-4 total rural road crossing. All mile markers are painted on middle of the pavement! We came from NC to get away from cold Jan weather---this trial was a perfect choice for two days of riding. Benches with bike tools and Trash cans are provided along trail. It was extremely clean! Although trail has some age, the pavement is not "rooty" I highly recommend this gorgeous 29-mile rail-trail ride! I just might come next winter for another two-day out-back ride on this trail!
Nice well paved trail. The new extension is particularly pretty.
We came in on the north spur and headed east. If I knew how bad the road was I would have been better prepared. We started out on hard-packed gravel which wasn’t too bad, but as we traveled east, the road deteriorated to a bumpy semi-paved trail. This was much worse than the gravel. We had to slow to 10-12 mph. After we let some air out of our tires, it was a little better but had to closely watch the road for bumps and holes.
Rode various portions of the trail over the course of three visits to complete the whole trail. From Killarney Station to Vineland-Apopka Station is still the best bike trail in Florida. Skip the part from Vineland-Apopka Station to Lester Road. Even so, this trail deserves 5 Stars
The Eastern part of this trail is paradise lost - some really spectacular views - it slowly becomes ugly the farther west you travel. Has some hills (for Florida lol) - it's nice to go in here to the shade after the Courtney Campbell. The only thing lacking is a water fountain and restroom. I'll do this trail over and over and enjoy the views everytime!
Rode from Green Pond trailhead and except for a few rain showers it was a great ride.
Beautiful trail. Started in Apopka and ended in Winter Garden where my girlfriend and I grabbed lunch and rode back to Apopka. Not many bikers for a Sunday afternoon.
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
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