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 Cross Volusia Trail and Neighborhood Lakes Scenic Trail. With more than 52 trails covering 442 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

General James A. Van Fleet State Trail

Van Fleet RailTrail

February, 2023 by jlwhitmer3

This was my first and last visit to this trail. Unfortunately the trail has deteriorated over the years. The tree roots have caused some serious and dangerous conditions to fellow bike riders. Some paint have marked these situations, but not enough to prevent accidents. The trail is so rural and the trailheads are not up to par to other trails in Florida. Sorry to be this negative but some attention to this trail is overdue.

General James A. Van Fleet State Trail

Love this trail

February, 2023 by kakcc

We’ll be back!

Withlacoochee State Trail

Lovely ride

February, 2023 by kakcc

We did 5 miles out and back starting at the bottom. Great asphalt and not too busy!

Accordion

Shingle Creek Regional Trail (FL)

beautiful quiet ride

February, 2023 by moritheblonde

We did almost 10 miles in this beautiful trail. Very well maintained and nice neighborhoods. Not crowded and easy to find.

General James A. Van Fleet State Trail

Great trail but sections badly need repairs

February, 2023 by klarson5

Great trail but sections badly need repairs.

Lake Apopka Loop Trail

Need a mountain bike with wide tires and shock absorbers to ride comfortably. Lots of birds, water fowl

January, 2023 by genedonaldson1986

Need a mountain bike with wide tires and shock absorbers to ride comfortably. Lots of birds, water fowl

East Central Regional Rail Trail

very clean and quiet

January, 2023 by moritheblonde

Rode 6 miles out and back. Very nice clean and not busy (we biked on a Monday) . Worth to drive to Space View Park to start.

East Central Regional Rail Trail

Very nice and quiet trail

January, 2023 by cyula330

As we are from Canada and brought our bikes with us, we tried this trail from 994 Enterprise Osteen Rd parking area and biked to the highway 95. Our ride was 45 miles round trip and the road was excellent condition. The scenery (mostly trees) was nice for mid January 77 degrees sunny weather. No picnic area found, few bench to take a break and no restroom found. Except at the start are. Overall it’s a great ride for exercise!

Withlacoochee State Trail

Great Trail

January, 2023 by smock2

Enjoyed our ride. Will definitely do it again!

General James A. Van Fleet State Trail

Great Trail

January, 2023 by smock2

First time, will definitely do it again. Started at the park and plan to start at a different trailhead.

Auburndale TECO Trail

Relaxing and easy to walk!

January, 2023 by mtrdqwdfnp

Parked on the end where the dog park is so that was a plus! Super easy walk… will definitely be back.

General James A. Van Fleet State Trail

Very nice trail could use some maintenance, but it's still great for a road bike. Much better than most roads in Florida.

January, 2023 by carbajal0282

Very nice trail could use some maintenance, but it's still great for a road bike. Much better than most roads in Florida.

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Accordion

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