Explore the best rated trails in Winter Garden, FL. Whether you're looking for an easy walking trail or a bike trail like the Cross Volusia Trail and Seminole Wekiva Trail. With more than 43 trails covering 400 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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 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...
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 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...
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...
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 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...
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...
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...
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...
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...
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 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...
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 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 Spring to Spring Trail connects a number of natural springs, parks, and friendly towns between De Leon Springs and Deltona in Central Florida. Although much of the trail is completed (22 of 26...
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,...
Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte Springs. This popular, well-marked, 14-mile route is...
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 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...
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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...
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,...
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 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...
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...
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 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;...
Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte Springs. This popular, well-marked, 14-mile route is...
In northern Orlando, the Gaston Edwards Trail provides a pleasant jaunt of nearly a mile along Lake Ivanhoe's eastern shore. (Hence, the trail is also known as the Lake Ivanhoe Trail.) The paved route...
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 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 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...
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...
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 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...
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 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...
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...
The Goldsboro Trail is approximately a mile long, located in the Goldsboro neighborhood of Sanford, Florida. The neighborhood was one of Florida's first incorporated Black communities but was annexed...
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...
The Spring to Spring Trail connects a number of natural springs, parks, and friendly towns between De Leon Springs and Deltona in Central Florida. Although much of the trail is completed (22 of 26...
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 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...
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 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...
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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...
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 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 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...
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...
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...
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....
In northern Orlando, the Gaston Edwards Trail provides a pleasant jaunt of nearly a mile along Lake Ivanhoe's eastern shore. (Hence, the trail is also known as the Lake Ivanhoe Trail.) The paved route...
The Lake Baldwin Trail is a 12-foot wide multi-use trail that circles Lake Baldwin in Orlando Florida. The asphalt trail is wide enough to accommodate different types of users, including older...
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...
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,...
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,...
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 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...
Rode the trail again but took the 47 mile route for my 1st CENTURY ride, just wish I could have gotten three more miles on that side for the full 50. The new addition to trail is nearly done but is accessible, just be aware of the incomplete curbs! Trail is mostly shaded until you get to Sanford’s Coast line which is beautiful¿. Came into close encounters with two baby bobcats at mile 92 as the sun began to set. Let’s say the adrenaline kicked in very quick. Warning there are three overpass so if you ride entire trail save some energy but you can skip the over pass and pass underneath for wimps only! SAFE TRAVELS!¿¿¿¿
This is more like an alley between what are not nice areas.. felt unsafe. Plus the pavement is in bad shape
We road the Clermont to Winter Garden part of the trail. It is one of the most scenic and nicest trails we road in central Florida. Highly recommend it. Start in Clermont, have lunch at the brewery building on the west of Winter Garden and return to Clermont. About 13 miles one way.
This trail is ideal for race training. If you’re looking to put your head down and pound it for 3-4 hours, then this is your place. If you’re looking for some hills and turns, or if you want sights there are better choices. This is very remote with no water options. Bring your own. We’ll go again but I like the Withalacoochee and Marjorie Carr Trails more.
This trail lives up to the hype...Winter Garden is top notch with all types of shops and restaurants...we’ll definitely do this again!
Nicely maintained, smooth trail through the wilderness area. We started out on the Good neighbor trail and the road north from there on Withlacoochee. Did 35 miles RT Total. Lots of shade and some nice benches or picnic tables. Yes, plan on drinking your own water, so pack accordingly.
Spacious Trails throughout lovely master planned communities and quaint downtown Lake Nona.Even connections that are not a part of the trail are fairly wide and an enjoyable ride.
Awesome, flat, straight trail (NO stops for roads/traffic). We saw lots of wildlife including turtles, snakes & a huge gator.
The trail winds around beautiful woods and a golf course with minimal exposure to traffic.
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
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