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 460 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

East Central Regional Rail Trail

fun trail

February, 2025 by johnpemble

I was amazed at the natural beauty of this trail. Very scenic from Edgewater going South. Restrooms in Edgewater were spotless. I liked it and would go again!

West Orange Trail

Decent Trail

January, 2025 by mgelsomino27

The trail is well maintained. There are a lot of road crossings and this in general is poor for road biking with only a few sections that are decent in length without interruption. For those using tri bikes there is essentially nowhere I felt comfortable in the aerobars. This is better suited for more leisurely activities.

Sanford RiverWalk

Scenic but short

January, 2025 by jmk355

Terrific trail along Lake Monroe. Fresh and smooth surface (mostly) and a relaxing ride. Only 4.5 miles long however, but does connect to Cross Seminole trail, albiet at the end with lots of traffic.

Accordion

Cross Seminole Trail

Tale of two trails

January, 2025 by jmk355

I began near the middle at Soldier's Creek Park. I erred in heading northwest with the goal of connecting to the Sanford Riverwalk. Although I made the connection (and loved the riverwalk next to Lake Monroe, I had to ride primarily on sidewalk/trail adjacent to busy roads and commercial districts. The green cross walks and occasional sign aided in following the trail, but I still ended up missing a couple of turns and needed to double back. I am surprised I didnt collide with any cars crossing into offices and stores along the way.
When I made it back to the park (mm 15.5 or so), I continued southwest and found it to be a terrific ride. Few cross streets, open riding and much more interesting scenery. Primarily residential, there were a number of parks, woods, creeks etc along the way. Unfortunately I was running low on sunlight and wasn't able to get to the end in that direction.
I heartily endorse riding this end of the trail. Save the northern end for Sundays or low car volume days.

Pleasant Hill Road Recreational Pathway

trail

January, 2025 by tholzapfel

Paved path runs parallel to the road the whole time. Park in lot at Walgreen’s because there’s no lot at trail head. It was ok.

South Lake (Lake Minneola Scenic) Trail

Closed Section

November, 2024 by mattmortefolio

As of 11/24, there was a roughly a1000 foot section of the trail adjacent to the lake that is still closed due to past hurricane flooding. You will have to go on the road to get around it. No longer flooded, just covered with debris which will hopefully be cleaned up soon.

Good Neighbor Trail

one of my favorites in Florida

November, 2024 by brookeypav

I’ve done this trail three times now on different skates. It’s on of my favorite trails on the Coast to Coast Trail & also just in general in Central Florida. It’s smooth. It’s beautiful and peaceful. Never too crowded. Currently open and only a small wet spot but manageable for skaters of quads and in-lines.

Fort Fraser Trail

No parking at Trailheads

November, 2024 by cindypearson2020

We were surprised to find no designated parking at either trailhead ends. We did discover a nice area at the Polk State College trailhead in Lakeland with picnic table. The trail was nicely paved except for a couple spots. Not very scenic but a decent ride.

Spring to Spring Trail

my first trail on an E bike

November, 2024 by mhchilds

Not the trail you want to do for you first ride. It was amazing. Did about 21 miles of it. Now other trails are going to be hard to match this one. Saw a lot of wildlife, friendly ebike riders and it was beautiful. Lots of curves, tree covers trails and places to stop. I highly recommend riding this trail

Good Neighbor Trail

Trail is open thru Brooksville

October, 2024 by sprinkhaan_1

The Good Neighbor Trail was completed thru Brooksville several months ago. It passes thru Tom Varn park (water, restrooms, shelter) and connects to the SR 50 trail going to Weeki Wachee. SR 50 trail also connects to the Suncoast Trail. It has opened up many possibilities for long rides. For example you could start at Blue Run park in Dunellon (Marion County) and ride south 80+ miles, one-way, connecting to the Withlacooche, Good Neighbor, SR 50, Suncoast and Upper Tampa Bay trails, all the way into northern Hillsborough County.

East Central Regional Rail Trail

Nice trail to start the coast 2 coast across the state.

September, 2024 by bobtobias

Nice trail to start the coast 2 coast across the state.

Old Fort King Trail

Only 2 miles is paved.

September, 2024 by catnim2615

Only 2 miles is paved.

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Accordion

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