Find the top rated walking trails in Leesburg, 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.
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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 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...
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...
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...
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 Little Econ Greenway trail is just one section of the Orlando area's many fine trails. features riverside recreation, picnicking, wildlife watching, and canoe trails. It also features a canal...
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...
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...
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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 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 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....
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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 nearly mile-wide...
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...
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...
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 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...
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...
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...
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 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...
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...
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,...
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 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...
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 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...
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 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 nearly mile-wide...
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...
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...
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...
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...
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...
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 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 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...
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...
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...
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...
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...
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...
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...
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...
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...
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 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...
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 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...
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....
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...
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...
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...
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...
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 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 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 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 nearly mile-wide...
Kissimmee is doing a great job with this Trail!. I enjoyed the connection ride from Shingle Creek to Kissimmee Loop Trail That BRIDGE OVER John Young Parkway is a MUST, very pretty and a fun ride. Plenty of places for pictures, and selfies. Loved the ride alongside the creek. I will submit pics as soon as I download them. Can’t wait to see more connections added to this project. Tip: get there during the earlier part of the day. The roadway to get there is busy with traffic.
We started our ride at the Killarney Station. There are rest rooms there as well as a place to rent bikes. We rode to Winter Park, which is about 5 miles, where we stopped at Crooked Can Brewery. There are many eateries there too. We continued our ride another 4 miles before heading back and enjoyed the varied scenery. Although the paths are paved and wide and primarily flat, there are a number of rolling hills that added to our workout. As we finished our 18-mile ride, this seemed more evident.
We rented our bikes at Killarney station and rode past Winter Garden. The trail was in good shape. We wound through neighborhoods lined with Live Oaks and Sycamores. The weather was perfect and the trail is mostly shaded and protected from strong winds. We rode on a Wednesday so it wasn’t too crowded. Highlights were the cute towns of Tildenville, Oakland and Winter Garden. Can’t wait to ride it again!
This is a wonderful trail for biking, running, dog walking, etc. great for road bikers and mountain bike trails galore off the paved trail. Everyone in Marion country should try it & you’ll be coming back as often as you can.
Pros: easy access, clean, well-maintained and numerous restroom/pit stop/playground areas, Winter Garden (cool town with lots of energy), varied scenery (neighborhoods, town, golf course, highway frontage section, ball fields), great for families, excellent trail markings (if you got into trouble or have a mechanical, it is very easy to tell someone where you are).
Cons: if you’re a serious cyclists there are too many slow sections (through town) and intersections to post a solid effort, two sketchy areas where it wouldn’t be wise to get off your bike, crowded in parts (not dangerously though-folks we passed were respectful and moved to the right), the northeast end of the trail was not well marked and we couldn’t figure out if we were lost or the trail had ended.
We are avid cyclists and have thoroughly enjoyed this trail two times in the past year. The trail is well-maintained and we saw park patrol out and about during both of our trips. If you’re looking for a solid workout this trail is perfect. Minimal traffic, only a few intersections to cross and flat as a pancake. There are restrooms at both ends of the trail and at least one in the mid-point of the trail. Water fountains are sparse so make sure you’re carrying nutrition and plenty of water.
They have opened the section that joins the two pieces shown on the map. Thus one can join the trail at the Tapestry development off Dyer Blvd and go all the way to Kissimmee Lakefront or to Pioneer Village. Great addition. Looking forward to them finishing off the northern section up to Osceola Parkway next as they acquired the easement rights in 2018.
This beautiful trail has 4 parking lots @ the 0-10-20-29-mile markers. On 1Jan, Tom and I rode from Mile 0 @ the Polk city parking lot to Mile-15 out and back. We saw several box turtles and a few Gators in the water! On 2Jan we parked @ the Mile-20 Parking lot. Rode out and back to the 29-mile marker, then back to the 15-mile mark out and back! We saw quite a few more box turtles sitting out front of their burrows; if I parked bike and tried to get close for pic, they would quickly scurry back into the burrow! We enjoyed watching one cross as fast as she could from the opposite side of the trail back to her burrow... Saw a gator happily sunning self on side of trail! This trail rides primarily alongside a swamp on both sides... it is awesome if you like a natural setting with only 3-4 total rural road crossing. All mile markers are painted on middle of the pavement! We came from NC to get away from cold Jan weather---this trial was a perfect choice for two days of riding. Benches with bike tools and Trash cans are provided along trail. It was extremely clean! Although trail has some age, the pavement is not "rooty" I highly recommend this gorgeous 29-mile rail-trail ride! I just might come next winter for another two-day out-back ride on this trail!
Green Spring Park to Trail Bridge in Osteen - 5.3 miles (seemlessly continues from Trail Bridge), Osteen to Guise Road - 2.7 Miles about 8 miles..
Great Ride, well maintained trail. No Trailer parking at Green Springs Park but trailer parking available next door east at boat ramp parking. Not many people given it was New Years Day, beautiful place to explore..
I started at Lake Beresford Park which has a loop trail good for maybe 2+ miles. Head south towards Blue Springs which is an interesting place especially viewing the river & watching the manatees swim around where you could otherwise swim in summer. Surprisingly lots of people at the park for a weekday morning. Further down the trail there was some construction going on to extend the trail; after that riding on a wide sidewalk for mile or 2. I'm not sure how you'd get to the southern section via bike because of very busy road in DeBary.
So I packed up the bike & drove to Monroe Park and headed north & east. First few miles were very scenic over a boardwalk. The trail is good until just after Gemini Springs where it parallels a very busy road for a few miles but becomes a peaceful, scenic trail by the time you hit Green Springs. Here is meets up with the East Coast rail trail that goes another 7 miles or so to the gap.
It will be nice once this trail is continuous and also connects up with short stretches in DeLand where there's a lot of jumping around on sidewalks, trails, roads, etc. Some signs would be nice to help navigate. All-in-all a nice trail but needs connectivity work.
We started in downtown Titusville at the bike shop where we rented hybrids. The "trail" was hard to find from there because that part of it is riding on streets with marked bike lanes. Once on the trail it was fine; smooth & flat riding first through suburban housing & commercial development; then out into lush vegetation on both sides.
There was one bench to sit down at but otherwise out to Virgie's stop there was no place to sit/rest, get a drink or relieve oneself. Thankfully there was no rain or hot sun to contend with.
I hear there are stops as you go further west towards Osteen. It will be nice once the short gap is closed so you can go from either Edgewater or Titusville to Deltona and connect up to Spring to Spring trail.
Back in Titusville you're again on marked streets, then you can go over the Max Brewer Bridge on pedestrian sidewalk--nice view of the water or maybe a rocket launch. Not much beyond that for now.
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