Looking for the best trails around Winter Garden?

Explore the best rated trails in Winter Garden, FL, whether you're looking for an easy walking trail or a bike trail like the Withlacoochee State Trail and Cross Volusia Trail . With more than 52 trails covering 450 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.

Recent Trail Reviews

Seminole Wekiva Trail

Too much traffic!

February, 2024 by gjprutgers1978

I started this trail at the southern entrance. I got less than 3 miles into my bike ride and turned around. Too many intersections with heavy traffic. Perhaps this trail is better towards the northern end.

Good Neighbor Trail

2/26/23 trail closed BUT…

February, 2024 by crckco

Parked at historic train station. Headed east and after a mile or so found the trail is closed by Duke Energy to update electrical poles. Back to the truck, reloaded our bikes and headed to Mondon Hill Road and parked the truck. Took off for Withlacoochee Trail. On the return ride we spotted a fox squirrel, a hawk having dinner, and a free range chicken. Nice ride!

Marjorie Harris Carr Cross Florida Greenway (Santos Trailhead to CR 200)

cross trail

February, 2024 by denismegan2

Agree with all the comments on beauty. No place to buy food or beverages on the trail. Several picnic sites. Only use bottle water dispenser not hoses for water

Accordion

Orlando Southeast Trail

Great Ride during the Holidays

February, 2024 by jallen1804

I ride this area at least twice a week. The trails are wide & the scenery is pretty good. It is great place to ride at night if you enjoy that. The neighborhood is always well decorated at Christmas.

Hancock Trail

Hill work

February, 2024 by vbellatplay

On our visit to Florida and first time in the saddle in six months we opted for a short day, about 20 miles. We parked at the Copper library which was convenient and had nice bathrooms and water. There are new developments and a shopping complex since the details to this trail were written. At about mile 5 there is a Publix, Starbucks and a few more retail stores. There were a lot of roads to cross and hills to climb. We opted for a 6 mile round trip down the intersecting Lake Shore trail to Minneola Lake. That was a nice, scenic section. Overall a good day to start our season.

General James A. Van Fleet State Trail

Great Trail

February, 2024 by pdreger

Rode on a cold day but still saw otters and deer. Be careful because Google maps will take you the wrong way. The northern most part of the trail is in Mabel FL off Highway 50. The access road to this point is horrible but short.

Withlacoochee State Trail

e-bike

February, 2024 by moniquebangs

Had an excellent ride today. Nice trail, wide bike paths. Lots of bathrooms and picnic tables. Will go back.

Marjorie Harris Carr Cross Florida Greenway (Santos Trailhead to CR 200)

Top 5 Trail in country

February, 2024 by bethredeker1

This trail is just outstanding. There is just not enough you can say about it. We road only the paved part but it is beautiful. We saw deer and wild turkeys and even heard an owl. The trail is smooth and wide and everyone was very respectful. We liked the fact that has a nice mix of shade and sun. Also the fact that it has some moderate hills and how it winds through the forest is great. Highly recommend!!

Marjorie Harris Carr Cross Florida Greenway (Santos Trailhead to CR 200)

Excellent trail!

February, 2024 by childs01

My wife and I just did a 24 mile ride there on our ebikes. Beautiful wide and SMOOTH trails through the Florida woods. Many gentle hills and plenty of curves. Nice trail head with restrooms.

Withlacoochee State Trail

Great Trail

February, 2024 by suesettle08

We rode twice on this trail on Feb. 2-3 starting at the Central Motel in Inverness, FL. It is a very, very nice trail. We did 10 miles south from our motel and then rode from the motel north to the South Citrus Springs Trailhead, 26 miles round trip. Very busy on a beautiful Saturday morning with an even mix of recumbants, e-bikes and bikes - very few kids riding. When we go back to Florida next year, this trail and this motel are on the agenda again.

Seminole Wekiva Trail

Mileage

January, 2024 by sprinkhaan_1

The Seminole Wekiva has been extended a few times in recent years so you can find all sorts of claims about what the length is ... anywhere from 14 to 26 miles. I wanted to find out for myself, so I rode the entire length of the trail yesterday (1/26/24), noting my cyclometer mileage at various points, and compared that to the trail markers and what's listed on TrailLink.
I found that my cyclometer and the trail markers pretty closely matched each other. From MM 0 in Altamonte Springs (a little less than .1 of a mile north of SR 414) to the last marker on Longwood Markham Rd (17.75 miles), I believe the posted mileage is accurate. The Seminole Wekiva trail continues from the MM 17.75 marker onto the side path of SR 46, up to the Wekiva River and the Seminole/Lake county line, an additional .9 mile. My total mileage for the Seminole Wekiva trail was 18.7 miles, which is far short of the 26.5 miles listed in TrailLink. I think the 26.5 is including other trails which connect to the Seminole Wekiva as part of the total mileage. Beyond the Wekiva River the path is uninterrupted, but it is a different trail - the Wekiva Trail which is maintained by Lake County. I normally park at Neighborhood Lakes trailhead, which is off the Wekiva Trail about 6 miles west of the river. Similar situation on the south end of the Seminole Wekiva. Beyond MM 0 there is a wide sidewalk following SR 414 to US 441, about .7 mile. This is in Orange county and is supposed to be part of the West Orange Trail in the future, but I wouldn't consider it to be part of the Seminole Wekiva.
I usually don't ride the trail south of the San Sebastian trailhead because the crossings at 436/Laurel St. and 434/Orange Ave. are such a pain. Seminole county wants to build tunnels at both crossings which will help out a lot.
Overall, a nice trail with great connections to other trails!

Marjorie Harris Carr Cross Florida Greenway (Santos Trailhead to CR 200)

great afternoon tandem ride

January, 2024 by sandymo

We rode from Santos to the end and back. It’s a great trail and will only be improved as it gets additional length. An added bonus is the MTB trails that we’ll tackle tomorrow on our tandem 39er. Today we were on the road tandem.

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Accordion

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