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.
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 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...
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 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 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...
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...
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...
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,...
On its own, the Druid Road Trail is pretty respectable recreation trail. It’s nearly four miles long, paved all the way and is accessible to the many residents of Clearwater whose neighborhoods border...
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 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...
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...
This trail connects the Pinellas Trail in Clearwater to Clearwater Beach across the Memorial Causeway. It is a wide trail, separated from traffic as it slopes up Memorial Causeway Bridge. The trail...
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...
Neptune Road RecreationalPathway connects Kissimmee Lakefront to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee Lakefront Park and runs along the north side of Lakeshore...
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...
If you are looking for a picturesque stroll or a tranquil ride through nature close to an urban setting, then consider St. Petersburg’s Skyway Trail. The trail showcases the best of Clam Bayou’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 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 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...
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 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,...
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 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...
If you are looking for a picturesque stroll or a tranquil ride through nature close to an urban setting, then consider St. Petersburg’s Skyway Trail. The trail showcases the best of Clam Bayou’s...
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...
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 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...
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 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 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...
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 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 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;...
Panoramic views of Tampa Bay: That’s it, that’s the pitch for this recreational path at the southern tip of St. Petersburg. For uninterrupted views of the bay accessible by bike, this trail is hard to...
This trail connects the Pinellas Trail in Clearwater to Clearwater Beach across the Memorial Causeway. It is a wide trail, separated from traffic as it slopes up Memorial Causeway Bridge. The trail...
Neptune Road RecreationalPathway connects Kissimmee Lakefront to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee Lakefront Park and runs along the north side of Lakeshore...
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,...
On its own, the Druid Road Trail is pretty respectable recreation trail. It’s nearly four miles long, paved all the way and is accessible to the many residents of Clearwater whose neighborhoods border...
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...
Panoramic views of Tampa Bay: That’s it, that’s the pitch for this recreational path at the southern tip of St. Petersburg. For uninterrupted views of the bay accessible by bike, this trail is hard to...
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...
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 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...
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...
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...
Neptune Road RecreationalPathway connects Kissimmee Lakefront to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee Lakefront Park and runs along the north side of Lakeshore...
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 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 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...
If you are looking for a picturesque stroll or a tranquil ride through nature close to an urban setting, then consider St. Petersburg’s Skyway Trail. The trail showcases the best of Clam Bayou’s...
The Bayway Trail is a 3.7-mile non-motorized trail between St. Petersburg and St. Pete Beach, Florida. The trail begins its westward journey near the St. Petersburg southwest wastewater treatment...
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 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 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 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 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 first 2 1/2 miles would have been worth 4 stars but the unexpected short length puts it at 1 for me.
This is a pretty ride for sure and basically a nice facility. But the trail itself needs work is several spots. Way too many potholes are lurking and no evidence of recent patches.
I just rode this trail for the first time, and I have nothing but good things to say about it. In short, the ride is very scenic with a few challenging hills along the way. It's a nice alternative to the typically flat trails that I've ridden elsewhere in the state. The hills are really not that difficult assuming you have gearing. I wouldn't recommend this trail for single speed bikes though. There are a few major road crossings that you have to negotiate along the way, and I can see where pedestrians could be a hindrance while riding around the lake depending on the day of the week, but these are minor issues. I started my ride at Killarney Station at the east end of the trail which is a great place to begin. On the return trip, if you have the energy, you can continue past this point onto the West Orange Trail and ride a few more miles through Oakland into the heart of Winter Gardens (recommended). I assume at some point in time the west end of this trail will be extended beyond its abrupt ending since it will eventually be part of the Florida Coast-to-Coast Trail that will stretch across the state. I've ridden the Withlacoochee State Trail and the Pinellas Trail, and they are both great trails, but all things considered I found this trail to be a better biking experience.
Great ride on Ream Wilson trail! Lots to see, some shade and sun along the pathway.
I was surprised how isolated the trail was! It was very surreal !! Plenty of wild life and fresh air!!!
It was a beautiful ride however several sections are in need of repairs
As a long time user of the Withlacoochee State Trail I noticed the pavement over the past 10 years has been neglected. The paved surface is extremely bumpy and somewhat dangerous especially at the north end of the Trail. Passing other riders is dangerous because you never know when an edge pothole is going to take you out as you pass. In addition, it seems riders on this trail like to spread out making passing with available pavement dangerous. What ever happened to the rule "keep right". I would go somewhere else to ride.
This is a trail that I ride 2-3 times a week. A lot of times we will park on the south end at a Pizza Hut off of Rt 60 just a little west of the trail. It makes for a nice place to have lunch after our ride. The trail is nice, but is getting some rough areas that need to be repaired. There is a bike store on the west side of 98 that has a Saturday morning group ride at 7:30 that uses the trail, so, sometimes a bit of congestion. A lot of nature along the way, especially if you have an off-road bike, you can take a 1/2 mile paved spur that leads to the Circle B Bar Preserve. Beware, there are alligators in THEIR natural habitat.
Great urban trail! Smooth surface. No standing water after a rain. I explored the southern end from St. Pete to Clearwater. Wonderful pedestrian bridges over the major roadways made it easy to stay moving. However, the trail crosses quite a bit of traffic in and around Clearwater. Watch out for yourselves! Florida has the highest percentage of cycling deaths, per capita, in the US. I hope to further explore the trail in the future!
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