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...
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 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 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 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...
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 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 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...
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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 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 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...
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 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...
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 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 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 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 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...
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 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...
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...
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...
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 to the Pasco County line with the opening of a 5-mile section...
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 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 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 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...
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...
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...
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...
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...
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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 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 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...
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 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 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...
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...
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...
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 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 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...
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...
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 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 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...
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...
One of Florida's most popular and unique urban pathways, the Pinellas Trail stretches from St. Petersburg north to Tarpon Springs, and on to the Pasco County line with the opening of a 5-mile section...
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 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 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...
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 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 trail was fabulous, paved and winding along Lake Minneola. I would love to give our experience 5 stars, but several trail users made this impossible. We had been looking forward to biking this trail on our cruisers and traveled over an hour from Seminole County. We came on a Wednesday afternoon.
The posted speed limit on the trail is 15 mph and those directions are to also use the right side of the path.
Most of the bicyclists were riding touring bikes and exceeding the speed by a considerable amount. In addition, only two out of the more than 40 touring cyclists alerted us when they passed us. Because we didn't hear them coming, a collision nearly resulted in one case. We noticed that several pedestrians and a couple of other bicyclists were also startled at different times by these cyclists with some riding at speeds we've seen when they ride along the highway.
Another issue was people walking in groups spread across the entire path. I was nearly involved in a head-on collision with three cyclists because A walker who was spread across to the far left side of the trail did not yield despite my calling out 3 times "ON YOUR LEFT!" I had no where to go but into a pole or a park bench until she finally moved to her right. At that point I was able to see the other cyclists feet away who were only able to pass just inches from me. It could have been a big mess of bikes AND pedestrians.
Earlier we heard a jogger telling other groups to "break up" due to the same situation. No one walking seemed to hear him either.
I'd like to think that people just aren't thinking about how their use of the trail affects others. I really don't like to believe people are selfish and inconsiderate. Regardless of intent, however, there were at least three incidences that we personally witnessed or were involved in during our one and half ride in which we or others could have been hurt pretty badly.
In the interest of public safety it seems that the trail should be monitored, warnings given to abusers and fines imposed if they choose to continue to behave without concern for others.
Not a fun ride. Not sure how this is in the rails to trails guide, it would be fine if you needed to commute to work. All you hear is traffic and not much to see; trail is a little quieter once you get to the school. A lot of the pavement has roots, asphalt is in need of repair and there are poor transitions to the streets. Caution on the crosswalk as some cars ignore the crosswalk signal even while the lights are flashing. Lots of better trails to choose from in FL
Fun ride, well maintained paved surface. Several points of interest along the water. Saw nesting bald eagles. Nice to ride away from the highway noise. Highly recommend this beautiful trail.
The paved trail is pretty flat with the exception of some bridges across busy streets. From the parking lot at the Chamber of Commerce on the Winter Haven side to the end of the trail at W. Haines Blvd in Lake Alfred is 5.1m out and 5.1 miles back. It's pretty basic, but I would like to add some suggestions to make the ride slightly more enjoyable.
1) Try and time your ride for the third Saturday of the month. There is a free water ski show on Lake Silver. The show time changes so check the website for the Cypress Gardens Ski team. I suggest that you do your ride first and hit the show on the way back into Winter Haven as the bike path goes right past the lake.
2) Instead of just dead heading out to where the trail ends in Lake Alfred, take a little detour off the path to the Mackay Gardens and Lakeside Preserve. The preserve is a better destination than just the abrupt end of the trail in downtown Lake Alfred. It's about a mile east of the trail.
3) There's not a lot of shade on the trail so stay hydrated and bring sunscreen. There is a "splash pad park" along the trail in downtown Winter Haven where you can cool off under the misters so DEFINITELY bring a change of clothes.
4) Enjoy Winter Haven at the end of your ride. Again, bring a change of clothes...and explore the downtown area. There are public restrooms for changing near the splash park for changing. They have nice restaurants, coffee shops, a brewery, antique shops for browsing, and live music on Saturdays (once Covid subsides) - It's a cool little area to walk around after your ride.
I think it's a great way to kill a Saturday afternoon if you're looking for a leisurely ride. A good portion of the trail is through industrial areas, which is to be expected as this was an old train track bed, but if you're looking for a nice 10 or so mile easy trail, this is a good option.
Beautifully laid out trail with benches strategically placed and restroom facilities. Fabulous area to view nature in all its glory!
Great little trail with plenty of shade, ample parking and spectacular sunset viewing opportunities from either of the county park trailheads.
The trail is paved and there are great views the entire way. There are parks along the way and places to eat. Such a relaxing and beautiful ride.
I live 5 min from this trail and my family and I have gone bike riding and running on it. I just picked up roller blading as a way to change up my fitness. If your into biking and running this is the trail for you but if you like rollerblading I would recommend another trail. I parked in the fitness parking lot and skipped going over the bridge. I would rank the road here about 6/10 lots of cracks in the road and the pavement is uneven in most places I would assume because of tree roots but it’s still good for rollerblading. I made a right at the crossroads to head toward the dump. This part of the trail is terrible. Very rough for rollerblading.
We used the new, temporary parking just off 2850 List Road, the entrance to the only on weekends Wildlife Loop for cars. This temp lot is open daily and you can walk your bike through the opening left at the gate. However, the wildlife on the trail and the fact that it's closed to cars during the week makes up for it. We rode to Limpkin Point. The trail varies in comfort, sometimes a bit rocky, definitely not for road bikes. We took about an hour, stopping to see the wildlife and scenery. There are clean port-a-potties at the pump house and close to the trail entrance.
Visiting Orlando, first time we brought our bikes. Looked this up on the App. Enjoyed the rides on the well paved trail. Overcast February day, so sun was not a problem. Great warm up ride for a casual 1 hour ride out and back.
FFYI - was there on the weekend. The start of the trail on W Cypress St is closed, suggest you park in Courtney Campbell parking sites to walk the later part of the trail
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