Find the top rated walking trails in Winter Garden, 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 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,...
Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's northern neighborhoods. It winds by several lakes,...
Neighbors in Avalon Park will appreciate this short local trail - a place to walk, bike and meet that's right on their doorstep. The trail runs just short of a mile east from the trailhead on Mailer...
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 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 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 Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Coy Drive in Orlando, just past the Fashion...
Gertrude’s Walk spans three city blocks in downtown Orlando, providing access to offices and the city’s sports arena not far from its southern end. The trail runs adjacent to an active CSX and Amtrak...
The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. The trail offers riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a...
Kewannee Trail is a charming, neighborhood trail in Maitland, Florida. More than just a recreation path, the trail is popular as a connective line from the neighborhood to several destinations...
When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...
Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping. The first segment...
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...
Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the Cross Seminole Trail provides crucial residential links in this...
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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 US 92 Trail travels across northern DeLand, closely following the north side of the highway known locally as International Speedway Boulevard because it passes the famous racetrack at Daytona...
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 Titusville Multi-Use Trail, also known as the Wuesthoff Trail, is a short and pleasant paved path located in the southern outskirts of the city of Titusville. The trail runs through Wuesthoff Park...
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 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 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 Cross Volusia Trail will one day link the east and west sides of Volusia County, stretching 20 miles from Lake Beresford to the coastal city of New Smyrna Beach. Currently, it runs through 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...
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...
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,...
Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's northern neighborhoods. It winds by several lakes,...
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 US 92 Trail travels across northern DeLand, closely following the north side of the highway known locally as International Speedway Boulevard because it passes the famous racetrack at Daytona...
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're traveling to central Florida, you won't want to miss the Spring to Spring Trail, which connects a number of small, friendly towns between Orlando and Daytona Beach, as well as many of the...
A rail-trail that's a bit wild and off the beaten path, the Flagler Trail runs for around fourteen miles through rural Seminole County, to the northwest of Orlando. Nearly the entirety of the trail is...
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...
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...
The Titusville Multi-Use Trail, also known as the Wuesthoff Trail, is a short and pleasant paved path located in the southern outskirts of the city of Titusville. The trail runs through Wuesthoff 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...
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...
This is a paved multipurpose trail connecting two cities in central Florida. The pathway stretches 3 miles from W Main St. in Tavares, parallel to US-441 S, and terminates just after Kinne Pearce Rd....
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 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 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...
Neighbors in Avalon Park will appreciate this short local trail - a place to walk, bike and meet that's right on their doorstep. The trail runs just short of a mile east from the trailhead on Mailer...
This is a paved multipurpose trail connecting two cities in central Florida. The pathway stretches 3 miles from W Main St. in Tavares, parallel to US-441 S, and terminates just after Kinne Pearce Rd....
When complete, the East Central Regional Rail Trail will extend more than 50 miles between DeBary and Edgewater with another segment to Titusville. The trail will connect urban centers with the...
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 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...
Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods to schools, parks and shopping. The first segment...
The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. The trail offers riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a...
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 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,...
Bike, walk or jog along a safe separated multiuse path along State Route 415 between Osteen and Sanford. Points of interest include the East Central Regional Rail Trail (at the SR 415 trail’s northern...
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 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...
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The Marjorie Harris Carr Cross-Florida Greenway is on a mission to create a non-motorized conduit stretching 110 miles from the Gulf of Mexico to St. John’s River in Palatka. The corridor showcases...
If you're traveling to central Florida, you won't want to miss the Spring to Spring Trail, which connects a number of small, friendly towns between Orlando and Daytona Beach, as well as many of the...
The Sanford Riverwalk Trail follows the shoreline of Lake Monroe in Sanford, FL, north of Orlando. The riverwalk extends from US 17-92 to Mellonville Avenue and is one of the most scenic paved trails...
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...
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...
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...
We started at the golf club. We only rode this trail for a very short distance - but what we did see the trail was absolutely beautiful. It was too challenging for my wife and I - we are in our mid 70s. Glad we gave it a shot. (Wish we were 10 years younger!
I pick up the trail at Destination Parkway and go all the way up to Oak Ridge (3 miles total). It's well maintained, and really quite beautiful and peaceful. I incorporate these two sections into my daily ride and love it every time! The Destination Parkway to Sand Lakr road section is 1 mile along a canal setting. Lots of Sandhill Cranes to be seen, and some snakes (be careful, they're pretty venomous), but never any gators, which I have seen on the Sand Lake to Oak Ridge section (2 miles) in the lakes/ponds. This is a popular multi use trail, so be aware of people walking/running.
Trail is in great shape.. nice view as you ride.. It is very short 8.5 mile round trip..
Trail is average.. no much to see.. 90% of the trail is next to a busy road... Trail is not road bike friendly... ok if you have mountain bike.. I will not recommend!!
Great for biking, skating, running, walking you name it. Nice wide paved path so there’s room for everybody. Scenic ride along the water with fun spots over and under bridges. Lots of benches and water fountains to stop at along the way.
Cycled the full trail North & South today for the first time:
Trail is extremely well maintained, with mileage markers, and water & restrooms at terminus points. Incredibly scenic. Tons of wildlife! Mostly shaded. Very courteous visitors when passing in both directions, and from behind.
Here's my main concern: Deer.
I was riding early on a Sat morning, on the trail from about 8:30 A.M. to 11:00 A.M.
I had TWO very close calls of deer leaping out of the forest, crossing directly in front of me. First incident was two deer about 40 yards ahead. They crossed, then two more turned around just as I passed the point of the first crossing. Second encounter was only about 10 feet in front of me! A true Yikes! moment. Had no time to react whatsoever, a large deer bounded out and across the trail. Luckily we didn't collide. I was riding about 18 mph, not overly fast (or slow). I'm curious if other cyclists have had similar encounters. Crashing hard on the trail would potentially be serious, since help may not arrive rapidly. Also passed about 10-12 other deer just off the trail. I'm wondering if there was some kind of herd movement today that explained so many deer sightings/encounters inside one single ride. Any additional experiences would be helpful, as I surely want to continue riding this otherwise wonderful cycling heaven trail.
I truly enjoyed myself. I rented a bike from West Orange Trail bikes & blades...amazing customer service by the way, and took off to the trails. I saw so many beautiful surprises; peacock ¿, a snake slithering pass my bike ¿, etc. the trail had walkers, joggers, rollerbladers, and so much more. Heavenly covered with trees if you’re not too big on direct sunlight. I love my experience every time I go¿
We rode from the withlAchoochee state trail to the opposite side in brooksville. Great ride, we packed a squeeze bottle with electrolytes in water and I have the camelbak mule 3L of water. I thought that would be sufficient to ride there and back. We also had 4 miles to go at the start and finish as we put in at the trailhead just north of 50. In total 28 miles. The brooksville end is supposedly in a place that isn’t the best part of town but having the bathrooms and shops near was a real pleasur. If you do this ride, it is absolutely necessary to have plenty of water as there isn’t a drop available for 19
Road the trail today. 11 miles into the trail as you cross maytown road the trail is under water. Prevented me from getting to maytown spur. Beautiful ride. Sun and shade.
I come here every morning to run and rollerblade and it’s amazing. Although, it’s not long it is very good pavement to rollerblade!
So much fun! Dirt road along the river to the bike trail. Easy paved trail along the river. Saw wildlife. Loved the trail
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