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 37 trails covering 375 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.
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...
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...
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...
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...
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 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 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...
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 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...
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 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...
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 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...
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...
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 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...
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 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...
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...
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...
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...
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 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;...
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 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 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 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 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...
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...
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 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 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...
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 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 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...
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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...
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...
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...
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 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...
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 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 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...
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...
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...
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 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...
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 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 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...
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....
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...
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...
Once again, I have to tip my helmet to the people planning Florida's biking system!!! I have ridden (and reviewed ) some of the other trails on the planned cross Florida route. The MHC is another shining example of what a State and counties can achieve!!! What a great use of taxpayer money!!! The trail in very well maintained. Very clean. The ride is varied with hills, dense forest, curves, a newer growth forest-all on a nice wide , smooth path!!! I did the 33 mile round trip and am looking forward to the extensions that are planned in the future!!!! Bravo!!!
Drove over an hour to do trail - and it’s closed!
We rode from the Lake Monroe Park TH at the southern end near I 4 expressway to Gemini Springs. My wife is not an experienced bicyclist and does not ride longer distances or on the road. She loved this trail! It is very scenic with shaded board walks or smooth asphalt surfaces. It is moderately busy with cyclists, walkers and skaters. The people are courteous + unusually friendly. We had several great conversations when asking the locals for information. Past Gemini Springs it becomes more suburban along roads, but the initial portion is mostly wooded. We turned around and drove to Green Spring which is beautiful but emits sulfur odor.
This was the first time I have ridden the trail all the way from New Smyrna Beach to Titusville. Overall the trail is flat, straight, and the pavement excellent. There are very few road crossings in the Volusia County portion of the trail. But in the Brevard County portion, there are many road crossings, some that are very treacherous. Also there are benches along the trail in Volusia County and none in Brevard County. Much of the trail is through the woods and beautiful but as you get to Mims the trail parallels US1 and is not nearly as scenic. Overall, a great place to ride if you use caution on the crossings in Brevard. Being flat and straight, it lacks a signature feature like a tunnel or viaduct. There is really nothing that makes you want to go and ride the trail as a destination. I give it 9 gears on a 10 speed cassette.
All I can say is it is definitely worth the trip. Beautiful trail, well maintained and friendly people.
I share the same sentiment of many reviews made already. I will take partial credit for not reading the description of the trail in full detail. I had no idea that the trail disconnects in many places and expands through heavy traffic. I also drove an hour to get to this trail, looking forward to 22.8 miles one way as opposed to 22.8 round trip. Very disappointing.
Great trail with lots of curves and hills to keep it interesting.Also a lot of shade and few road crossings. Other then Santos trail head there is no water available which can be an issue. Bike rentals available at Santos trail head.
First bike trail I’ve ridden since moving to Florida. I really enjoyed this one. Goes past the Kissimmee Historic Society, & it’s a very scenic ride.
2019-03-05 Beautiful Saturday allowed me to enjoy an equally beautiful bike ride through this trail - which by the way can connect to Casselberry Trail ( if you want to make it a longer ride experience) I enjoyed the scenery. It is an easy Walk, Skate, In-line Skate, Jog or Bike Ride Come check it out for yourselves :-)
We started at the south at the Polk City trailhead and traveled north. The trail quickly goes into rural and then mostly wild surroundings on both sides of the trail. Looking at the maps, you can see the wildlife management area, but the same type of flora is found earlier in along the trail. A few houses, and views over farming on the east side of the trail.
Make sure to go far enough to get to 'The Bridges' which are near Withla on Google Maps. We saw alligators, snakes and hawks, and a lot of other birds and lizards.
At several points along the way the trail split--but no signs. They have some nice kiosks but with no maps just a bunch of stuff about plants, etc. Nice but I need to have better directions--not just guessing or following other people. The "hills"aren't much but still a little variety from most of FLs flat trails, even with crampy legs the "hills" weren't much challenge.
The new western segment from Hiawatha Park about 3 miles out was very nice; hope they extend it beyond the little bike cul de sac. Overall a nice trail, except for lots of road crossings and lack of signage.
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