Looking for the best trails around Winter Springs?

Explore the best rated trails in Winter Springs, FL, whether you're looking for an easy walking trail or a bike trail like the Ponce Inlet Trail and Cross Volusia Trail . With more than 52 trails covering 449 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

Cross Seminole Trail

Florida Trail Winter Springs

April, 2025 by danb48978

Been walking the trail for seven years and trail is becoming more and more popular for homeless camps in the woods. Witnessed a man beating a girl. Had a man pushing a shopping cart screaming at me telling me I am walking the wrong direction. More and more trash along the trail and food on benches . All good things come to an end.

Auburndale TECO Trail

nice and easy

March, 2025 by mbdp2005

Easy straight trail and lunch at Margaritaville

General James A. Van Fleet State Trail

Great Trail to Get Away

March, 2025 by robfitzkc

Started at Green Pond Trail Head and headed North. As reported, the trail has some pretty big bumps and a few holes, usually near the edge. With the limited traffic on the path, it isn't difficult to avoid them but you do have to keep your eyes on the trail. On 3/28 there was quite a bit of tree trimming and brush consolidation in the 10 miles between Green Pond and Bay Lake and some heavier equipment was staging at the State Park garage near Green Pond so maybe they are going to fix it this Spring.

The 10 miles between Green Pond and Bay lake is a very nice mostly shaded ride through timber with swamp land on both sides. There are 3 bridges about 2 1/2 Miles North of Green Pond which provides a place to watch alligators (this is mating season so you see some but there's a bunch more as the grunt and talk...), enjoy the birds and quiet serenity. At Bridge 2 that day, there is a 10+ Foot alligator nesting with her (soon to be) baby alligators.

North of Bay Lake is very nice and shaded for the 4 miles we traveled (Total round trip of 28 Miles).

Some call this trail 'straight and boring.' I'd suggest that it is quiet and serene, and, because it is straight and wide, you can spend most of your time enjoying nature!

Accordion

West Orange Trail

Killarney station problem

March, 2025 by bannerman

I have seen so many close calls with small children and groups renting bikes and organizing standing on the trail when speeders come down the hill and fly past them. Killarney rentals should come out the side door and not directly onto the trail or slow the traffic down.

General James A. Van Fleet State Trail

Some work needed after Hurricane

March, 2025 by dougtarter

Great trail! But definitely needs some work after the Hurricane's North of Polk City. Trucks have created some dangerous dips/holes in the asphalt from the trail repair crews. BE CAREFUL. the Shade hides some of the obstacles.
You may encounter some equipment on the trail also during weekdays. Hopefully, it will get re-surfaced along this 2 - 3 mile stretch. I did NOT RIDE South of Polk City. Overall, a Very Nice trail. Will be back to 4 star trail after repairs.

West Orange Trail

Just a note about a small correction!

February, 2025 by bcdalland

Living in Apopka, I've been on portions of the West Orange Trail MANY times. Your description starts at the southern point at the bottom of Lake Apopka and ends with the words describing the trail ending at its southern point along Lester Rd. You should change the word "southern" to "northern". Otherwise, a nice description of a very nice trail. Thank you.

General James A. Van Fleet State Trail

This is a great trail through marsh and forest area. As many we met on the trail say. This trail feeds our souls...enjoy. we will be back.

February, 2025 by diannereiter

This is a great trail through marsh and forest area. As many we met on the trail say. This trail feeds our souls...enjoy. we will be back.

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.

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.

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Accordion

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