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 463 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

Old Fort King Trail

Only 2 miles is paved.

September, 2024 by catnim2615

Only 2 miles is paved.

Withlacoochee State Trail

Trail is closed at the moment

September, 2024 by adamdb3600

Trail closed, drove to get here and found out with signs up at all the crossings in our area.

https://www.floridastateparks.org/parks-and-trails/withlacoochee-state-trail

West Orange Trail

Courtesy

September, 2024 by lahlonvance

I’ve ridden this trail several times. The trail itself is awesome. Not too many busy crossings lots of shade. I really like riding this trail. The one thing that takes away from the experiences too many bike riders who are very rude riding for too fast for this trail, walkers, people, walking, dogs, pushing strollers, etc., also passing in spots where they shouldn’t be running stop signs it’s getting to be where it’s almost dangerous

Accordion

Spring to Spring Trail

BH

August, 2024 by bhunt2660

It would be nice if some of you realized that E trikes are mostly used by persons that have limitations, there are so few ways that my husband can enjoy the outdoors, this is one way. Not all E bike/ E trike riders are inconsiderate. Thank you

Lake Apopka Loop Trail

Reptiles & Birds

August, 2024 by jallen1804

Bumpy ride, & snakes, alligators, egrets, herons, & hawks. A nice afternoon ride.

West Orange Trail

The trail is great but...

August, 2024 by webmail1

It's getting so dangerous with all of the electric mopeds I'm afraid to ride or walk on it.

General James A. Van Fleet State Trail

great trail

August, 2024 by loryad123

This is a great trail, beautiful shade. We saw deer, otter, a rat snake, and a pigmy rattlesnake. We love nature and if you don’t bother it, it won’t bother you. Lots of places to sit, as well as overview spots. Flat for most of the trail that we did. I recommend it highly

Cady Way Trail

For rollerbladers!

July, 2024 by bkmurphy

I am an average rollerblader and I very much enjoyed this trail. I gave 4 stars because there are a lot of road crossings, rumble strips and a bit of debris that you have to be careful of. Get there early though because there isn’t much shade and you will be directly under the sun as early as 8 AM. Otherwise, highly recommended for rollerbladers!

Sanford RiverWalk

Nice Ride on Weekdays

June, 2024 by jallen1804

The west end of this trail meets with the Cross Seminole Trail. You can cross the St John's River into Volusia County now. Good ride.

West Orange Trail

Great Trail

June, 2024 by wade.lanier

Scenery: 4/5
Shade: 4/5
Condition: 3/5
Crowdedness: 3/5
Amenities: 4/5
Road Crossings: 2/5
Signage: 3/5

This is a great trail, but it's not perfect. It meanders through several cute neighborhoods, towns, and wooded areas with a diverse array of pleasant scenery (woods, charming homes, open vistas, etc.). Stations and outposts all along the trail provide better amenities than most other trails. With just a few exceptions, shade is ample. The trail is very popular and can get quite crowded, especially between the end point at Killarney Station and the Apopka-Vineland outpost. Once you get past the Apopka-Vineland Outpost (heading east from Killarney Station) and turn north, the crowd really thins out and it's much easier to travel. Naturally, crowds are heaviest on weekends and when the weather is mild. The trail is in good shape for the most part, although there are places where it is noticeably bumpy due to root incursion. My biggest complaint is the number of road crossings - there are a LOT. Some of them are very busy with automobile traffic, and some of them are quite rough. All in all, though, it's a very pleasant trail, and I would certainly ride it again. It's important to note that this trail is relatively long. I have ridden the entire trail, and my observations apply to the trail as a whole. Some observations may not apply to certain sections of the trail.

South Lake (Lake Minneola Scenic Trail)

Among the Best in Central Florida

June, 2024 by wade.lanier

Scenery: 5/5
Shade: 4/5
Condition: 5/5
Crowdedness: 4/5
Water Availability: 3/5
Road Crossings: 3/5
Signage: 2/5

This is one of my favorite trails in Central Florida. In this area, the West Orange Trail is the most popular, but I think the South Lake/Lake Minneola Trail beats out in terms of scenery and crowdedness. Except for the portion of the trail that follows the shoreline of Lake Minneola, shade is ample. It is less crowded than the West Orange Trail, except for the portion that runs through the lakefront park on Lake Minneola. This is understandable given the nature of the park. The crowded stretch is manageable as long as you take it slow and are patient, and it's relatively short compared to the rest of the trail as a whole. The scenery both through wooded areas and along the lake is great. On the western end, the section through Lake Hiawatha Preserve is beautiful albeit very short. Beyond the Preserve (heading west), there's not much to see. The trail is in very good shape, but there are a good number of road crossings. Overall, a really great trail that, in my opinion, is more enjoyable than the West Orange Trail.

Hancock Trail

Description Says It All

June, 2024 by wade.lanier

Scenery: 2/5
Shade: 1/5
Condition: 5/5
Crowdedness: 5/5
Water Availability: 1/5
Road Crossings: 1/5
Signage: 3/5

Skip this one if you have better options. The description pretty much says it all: not much scenery (almost entirely suburban), hilly (for Florida standards), no water, no shade. On a clear day, there is some scenery at the northern end where you can see Lake Apopka and the Orlando skyline on the eastern horizon, but rampant development is quickly wiping that out. There are a lot of road crossings, some busy. Virtually all of the trail parallels a rather busy, noisy road. The trail is in good shape (except for a few spots where roots have created bumps - mostly on the southern end), but I'm not sure why the description says that it is 14 feet wide. There may be short sections where that is the case, but mostly not. The trail is not crowded at all, but, given its shortcomings, that's not surprising.

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Accordion

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