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 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...
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...
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 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 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 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 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...
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...
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 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...
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 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;...
This is a broad paved trail traveling within the Duke Energy powerline corridor, stretching 2.4 miles from the SR 54 to the Pasco/ Pinellas County line. This stretch of trail is actually strategically...
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 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...
The Coastal Aneclote Trail is a multi-use path is southeast Pasco County. The 4.5-mile trail provides safe bike-ped connections between the Pinellas Trail (via the developing Elfers Spur Trail) and...
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...
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...
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,...
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...
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...
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 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...
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...
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...
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 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,...
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 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 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...
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 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 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 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 Coastal Aneclote Trail is a multi-use path is southeast Pasco County. The 4.5-mile trail provides safe bike-ped connections between the Pinellas Trail (via the developing Elfers Spur Trail) and...
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...
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 Oldsmar Trail extends over 10 miles, and links to 10 major parks in Oldsmar, Florida. R.E. Olds Park lies at the center of the system, which is roughly shaped like an upside down T. One...
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 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 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...
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...
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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 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...
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 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 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 Coastal Aneclote Trail is a multi-use path is southeast Pasco County. The 4.5-mile trail provides safe bike-ped connections between the Pinellas Trail (via the developing Elfers Spur Trail) and...
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...
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...
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...
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...
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...
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 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 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 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 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...
Nice place to go since trail is shaded. Twigs and branches are in trail so difficult to inline skate at times. The bathrooms are filthy!!!
i have ridden this trail from both st pete beach and clearwater beach. my most scenic rides were from clearwater beach. first , to take advantage of the most scenic parks, get a free AAA map of the county. starting in clearwater beach, bike over to the bridge trail up to the pull off at the very top ,take in the view of the intracoastal waterway in both directions. wow,wow!!!!! at the end go right on the trail then left. in a short distance you will intersect the pinellas trail. this time i took a left towards Dunedin. along the way one could take a short detour to view the ocean. i continued straight ahead past a pretty golf course to dunedin. at the lights take a left on the trail along the ocean causeway . another wow!! to honeymoon island. where you can take in a swim or (since i love nature) go to the visitor center, lock the bike, and walk the sandy paths all the time watching osprey and maybe an eagle feeding their young. return to clearwater beach . only 20 miles, easy for a recreational rider like me(80 years) on a hybrid. equally scenic south on the pinellas trail. john taylor park,lake with alligators, walsingham park(lake with bike trail, seminole city park(pond with ducks),boca ciega park(boardwalk,high wooden tower overlooking the intracoastal. booring?????
Depressed area, abandon industrial complex, water treatment plants, Grave yards this is for you. Only for people that live there.
We have ridden most of the trails in central florida, most are beautiful, this one not so much. No shade and not much to see.
First time on the trail we started at the Croom area. Restrooms were well-maintained and we saw the deputy sheriff twice. I look forward to riding the complete 46 mile trail. Thank you everyone for taking great care of this trail.
Great ride for seeing wildlife. I’ve seen bobcats, alligators, panthers, turtles, birds, snakes, and more. The magnolia Park trailhead is closed but you can access the trail at the McDonald Canal or Green Mountain trailheads. Must use mountain bike as trail is mostly gravel. There are a few lookouts you can climb to get a better view of the area. There’s also quite a few covered benches along the way.
I ride this trail frequently. It’s a little congested by Victory Park (by the lake) with walkers and joggers, but keep going and it thins out dramatically. Nice, pretty, almost flat ride. A lot of the trail is through woods with limited houses along the way.
Beautiful trail. I did this with my son October 2020. Pretty much a straight run from st pete to Tampa. It runs along the side of a highway but zero danger. It’s separated by a shoulder and landscaping. You pass a few beaches along the way. There are a few bridges. Constant breeze through the ride over Tampa bay. Highly recommended.
This is our sixth trail that we have tried. Very smooth. Well marked mile markers. Not a lot of scenery. We went on a beautiful Monday in June. In the six mile trip we passed about 15 people. The people seemed very friendly. Much more so than other trails we’ve tried. Do not make a special long trip for this path. It would be a great trail if you’re in the area or live locally. As far as nature we saw lots of birds and four snakes. Harmless black snakes. Bathrooms were not plentiful and very dirty. No trash anywhere on the trail.
This is a wonderful trail just to see how far you can go. It’s 20+ miles of straightaway. The people are friendly and courteous as well. Minor animal spotting like gopher turtles and random non-venomous snakes.
We are 70ish and rode this trail on our ebikes. We RV and try to do a couple trails a week normally in the 25 to 30 mile range. We parked in Ben Carson Park. Paid parking about 50 cents an hour paid at a kiosk with credit card or change. We arrived at 0900 on Memorial Day and there was plenty of parking. We got back at noon and all the parking spots were taken and entrances were blocked. My advice would be to park at a park in Safety Harbor and bike that trail down to this trail. This will be one of our favorite trails and we will return. reason for us to take out a subscription
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