Explore the best rated trails in Leesburg, FL. Whether you're looking for an easy walking trail or a bike trail like the Cross Volusia Trail and Orlando Southeast Trail . With more than 47 trails covering 452 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.
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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...
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, 20-mile route is...
The Lake Underhill Path is a greenway linking four parks in Orlando near the Orlando Executive Airport in downtown Orlando. Work out stations dot the length of the trail, which is why you might hear...
Fountain Lake Trail is just short of a mile long, and occupies a former CSX railroad corridor. The trail is built to accommodate both pedestrians and cyclists, as well as other non-motorized users....
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...
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...
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,...
As its name suggests, the Leesburg-Wildwood Trail is planned to connect the two communities via an off-street, walking and biking pathway. Presently, the trail extends between Veech Road and N. 14th...
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 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...
With a final 3.5 miles paved in between Osteen and Farmton in 2021, the East Central Regional Rail Trail is complete. The trail extends more than 50 miles between DeBary and Edgewater with another...
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...
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...
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...
Located in Leesburg, Florida, this two-lane, asphalt trail parallels Canal Street, connecting to the Venetian Gardens Park at its southern end. The park is spread out over 45 acres tucked into 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...
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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 startled with humble beginnings of just over 1 mile, beginning...
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...
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...
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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...
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...
As its name suggests, the Leesburg-Wildwood Trail is planned to connect the two communities via an off-street, walking and biking pathway. Presently, the trail extends between Veech Road and N. 14th...
After 30 years of planning, the first segment of the Shingle Creek Regional Trail opened in Kissimmee in November 2016. The paved trail startled with humble beginnings of just over 1 mile, beginning...
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...
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...
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 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...
Lying largely within the Marjorie Harris Carr Cross Florida Greenway, this trail passes 2.5 miles through stands of cypress and across the Withlacoochee River over a magnificent new (in 2014) bridge....
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...
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...
Located in Leesburg, Florida, this two-lane, asphalt trail parallels Canal Street, connecting to the Venetian Gardens Park at its southern end. The park is spread out over 45 acres tucked into 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...
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 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...
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 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;...
With a final 3.5 miles paved in between Osteen and Farmton in 2021, the East Central Regional Rail Trail is complete. The trail extends more than 50 miles between DeBary and Edgewater with another...
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 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...
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, 20-mile route is...
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...
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...
Located in Leesburg, Florida, this two-lane, asphalt trail parallels Canal Street, connecting to the Venetian Gardens Park at its southern end. The park is spread out over 45 acres tucked into the...
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...
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...
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 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,...
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The Crosstown Trail in Crystal River is a historic railway line that has been converted into a multiuse trail stretching nearly two miles. The concrete trail is used for walking, biking and hiking. A...
This is a biking and walking trail located in Leesburg, Florida. It's the first part of what is hoped to be a rail-trail extending to Leesburg High School. Currently, the paved trail heads east from...
With a final 3.5 miles paved in between Osteen and Farmton in 2021, the East Central Regional Rail Trail is complete. The trail extends more than 50 miles between DeBary and Edgewater with another...
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 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 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 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 Withlacoochee Bay Trail extends from the Gulf, north of Crystal River and south of Inglis, nearly 5 miles east to just beyond North Suncoast Boulevard. The trail provides access to a 758-acre...
As its name suggests, the Leesburg-Wildwood Trail is planned to connect the two communities via an off-street, walking and biking pathway. Presently, the trail extends between Veech Road and N. 14th...
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 Lake Underhill Path is a greenway linking four parks in Orlando near the Orlando Executive Airport in downtown Orlando. Work out stations dot the length of the trail, which is why you might hear...
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...
Rode out and back about 50 miles from the Edgewater Rotary Park towards Titusville. The trail is in near perfect condition with only a few minor surface bumps within the first few miles. This is a great trail for training as it really opens up after the first 1/2 dozen miles or so and you can really roll if you like. The scenery is also pretty good too. No services other than an “honor” station so take what you need unless you’re going all the way to Titusville.
We started at south end in Polk City and biked 8 miles north. There is plenty of parking and a restroom about .5 mile in. Nice wide trail with benches along the way. Plenty of tortoises! We also saw turkeys. We crossed a dirt road and a major 2 lane road on this section. 1/2 mile markers are painted on the trail. Mostly shady and so quiet-only heard the birds. Asphalt trail was mostly smooth but did have some bumps and rolling areas. I would bike it again if in the area.
This trail now extends to the Spring to Spring trail at Lake Monroe Park. If you go East to Mellonville road then south on the road to route 25, you will find a sidewalk bike trail east to hwy 415. The on the West side of 415 another sidewalk trail extends into a full blown double lane trail at Celery avenue up to Osteen connected to the Rail to Rail trail. Head West and connect to the Spring to Spring south trail back to Lake Monroe Park. Roundtrip is about 30 miles around lake Monroe. Stops at Green Springs park, Gemini Springs park, Debary Hall, and Beck Ranch park.
This is one of the most naturally beautiful segments of trail in the area. That said, there are many segments that are not complete yet, and there are many segments that are showing their age, with treacherous rough surfaces, cracked pavement, potholes. The whole area could use some love, but it’s so beautiful. Better suited to walking/jogging than cycling simply because it’s twisty and worn out in places.
This trail now runs all the way to the county line, across the St John’s River at 17-92 and connects to the Spring to Spring trail. It is possible to begin in downtown Sanford, followed the trail west and head north across the Saint John, Loop back east and follow the trail to Osteen, and on to Edgewater or Titusville, if you’re feeling adventurous, or head south at 415 in Osteen and back across the river. You will have to follow Celery Ave for two miles, to Melonville, But it is a roughly 26 mile loop around the lake with 24 on dedicated trail.
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!!!
Beautiful riverwalk, now extended all the way to the Sanford Zoo. Plenty of seating and scenic views. My favorite place to run!
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.
This trail has a lot of potential. Unfortunately, there is a lot of litter and homeless. Do not use this trail by yourself.
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.
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