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 Orlando Southeast Trail . With more than 48 trails covering 423 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.
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...
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 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...
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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...
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 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...
This trail branches off from the Leesburg-Wildwood rail-trail and will some day reach Fruitland Park, about 3 miles away. The current paved portion extends 0.7 miles, cutting a shaded swath past...
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...
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...
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 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 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...
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,...
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...
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...
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...
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...
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...
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...
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,...
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 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...
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 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 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 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...
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 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...
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...
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...
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...
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 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...
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...
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 startled with humble beginnings of just over 1 mile, beginning...
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 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 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 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 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...
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 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 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...
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 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 Neptune Road Recreational Pathway, also known as the Bill Johnston Memorial Pathway, connects Kissimmee's Lakefront Park to St. Cloud in central Florida. The 10-foot wide trail exits the Kissimmee...
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 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...
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,...
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 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...
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...
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...
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 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;...
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...
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!
Depressed area, abandon industrial complex, water treatment plants, Grave yards this is for you. Only for people that live there.
We have ridden most of the trails in central florida, most are beautiful, this one not so much. No shade and not much to see.
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.
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