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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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 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 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 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 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...
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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 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...
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...
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...
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 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 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...
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 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 Good Neighbor Trail will some day run 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. 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...
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 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,...
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...
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...
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,...
The Good Neighbor Trail will some day run 10 miles from Brooksville to the Withlacoochee State Forest in western Florida, following the route of the former Florida Southern Railroad Line. The...
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...
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 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 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...
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...
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 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 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 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 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...
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 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 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...
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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 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 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 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...
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 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 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 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 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...
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...
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 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,...
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...
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 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...
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 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 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.
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
The Upper Tampa Bay trail is a 'go to' ride for many reasons. Multiple access points within parks, a 'no-cost' parking option at the Citrus Park Mall (1 block from trail), a nice bike shop along the route across from a Tiki Bar style restaurant that will quench your thirst as desired. The route has contour following a waterway, street flyover to let your shift gears and climb the small hill, and plenty of shade along the route for the warm Tampa days. A good mix of riders, walkers and runners can be found throughout the day. The trail is quiet and safe - highly recommended!
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”.
A great ride across the upper Tampa Bay. In the early morning you will encounter groups of serious riders, runners etc. In the evening you'll see many people fishing, roller blading or getting ready for the sunset. The bridge at the halfway point is a fun/challenging/scenic distraction as well. Only downfalls are loud traffic nearby and no water stations. Certainly one of the better rides in Tampa though!
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.
Great road & mtb trails, very easy and fast.. Only down fall is any kind of rain will end the ride.. trails flood very easy even the road loop.
Trails hold water for a long time, you can count on any kind of rain closing the trails for a couple of weeks.
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
Rode this for the first time today. Byclists were freindly/respectful of one another. Wild life to see and water stops were good. A $2.00 fee was fine if it helps with upkeep. Put this on your list to ride!
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