Looking for the best trails around Webster?

Explore the best rated trails in Webster, FL, whether you're looking for an easy walking trail or a bike trail like the Withlacoochee State Trail and Neighborhood Lakes Scenic Trail . With more than 54 trails covering 592 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

Withlacoochee State Trail

Beautiful trail!

April, 2025 by kakcc

We parked at Lake Townsen Park, had some lunch at Bree’s Provisions (They close at 2:00) and rode north, out and back for about an hour. The trail is well maintained and goes through beautiful farm country.

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

Accordion

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!

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.

Pinellas Loop Trail

What a beautiful day on this part of the trail... well maintained, some many places to stop, site seeing, Sponge Docks, Monkey Farm, Shopping, Restaurants and libations.

March, 2025 by gmcplc79

What a beautiful day on this part of the trail... well maintained, some many places to stop, site seeing, Sponge Docks, Monkey Farm, Shopping, Restaurants and libations.

Starkey Gap Trail

sTARKEY gAP tRAIL

March, 2025 by donnatraficante

The trail and the land needs to be cleaned up. The grass and weeds needs to mowed and garbage in the grass. The weeds are as high all along the trail by Trinity Blvd. You have a nice trail but the surrounding areas are filthy. It makes the homes /townhomes look shabby. How come Starkey doesn't have weekly maintaince on this empty lot???. She made promises when she was running telling us that this is going to be beautiful. Why not put some lights up for the darkness when walking or riding on this trail?????? The area around this trail is filthy and needs attention Asap!!!!!!

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.

Fred Marquis Pinellas Trail

Trail along major highway.

February, 2025 by cindypearson2020

We started at the Pinellas Trail North, the beginning point, and rode 10 miles out to John Chestnut Park. The first 2.5 miles runs alongside a preserve so quiet, scenic & very family friendly. The rest of the ride was along the highway so continual road noise although every major intersection had a button for the crosswalks, the trail is well paved & wide. There was no signage for parking at the trail head or restroom facilities. Signage to guide you to Tarpon Springs is also very limited.

Starkey Gap Trail

smooth and great for intervals

February, 2025 by stephaniearias702

Training for a sprint Triathlon and used this for interval training. Not much shade but the perfect length for beginners and early training.

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Accordion

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