Looking for the best trails around Roscoe?

Explore the best rated trails in Roscoe, NY, whether you're looking for an easy walking trail or a bike trail like the Hudson River Brickyard Trail and Lackawanna River Heritage Trail . With more than 33 trails covering 314 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

D & H Canal Linear Park and Towpath Trail

Texas Chain Saw Trail

August, 2025 by jilliantor23

The trail was really nice if you went towards Wurtsboro, butttt we originally made the mistake of going the other way and wound up at the Texas Chain Saw House. I thought we were going to be killed by a rapid dog. The trail was very confusing, maybe we weren't going the right way??? It did look like the trail indicated to go straight, but there was a car parked in the middle of the trail and crazy dogs not fenced and only on a rope. I thought it would get loose and tear myself and my dog apart. There's got to be better markings. Or someone needs to figure out a way to make this homeowner happy, because clearly he is disgruntled.

Heritage Trail (NY)

great trail , great maintenance , would recommend

August, 2025 by campinfool

What a wonderful ride , we did a total of 30 miles from Middletown to Chester and back ! Awesome trail wonderful maintenance of the trail!! Would recommend to anyone that wants to ride Loved the many Jonny on the spots and benches along the trail! As well as eating and drinks along the way to buy ! Even a bike repair station on the trail!!!! ¿¿¿¿ Kevin & Pat Bennett

Ashokan Rail Trail

beautiful ride

August, 2025 by campinfool

Awesome ride !!! total 24 miles just breathtaking !!! Trail was wonderful mostly flat , busy with walkers and bikers all friendly !! Pat &Kevin Bennett

Accordion

D & H Canal Linear Park and Towpath Trail

Great start from Wurtsboro ... but then THIS!

July, 2025 by jason.harry

Sunny and warm July Sunday. Started from the handy parking spaces across from the Wurtsboro firehouse (corner of Pine St. and Canal St.) The informational signs in the little park back toward Sullivan St. are worth checking out before heading north on the trail.

The trail is really nice in that beginning stretch: some gravel, mown grass, hard dirt. Easy on a hybrid or mountain bike ... probably too rough for a road bike. Riding along the long-forgotten, but still totally visible, D&H canal is very pleasant. Some lengths of the canal itself are totally dry and filled with mature trees; other lengths have water. (We didn't stop to read them, but there is fun signage along the way that tells a narrative story about the area.) Mixture of shady tree coverage and open skies. Very, very nice!

BUT THEN! Big surprise. As the towpath crosses McDonald Rd and continues north, which is maybe only 1 mile from the start, the bike path is fully flooded by water and completely unpassable. This is due to a total blockage of water in the canal by a massive beaver dam. (This is right where a home, yard, and outbuildings are visible on the satellite view. And, yes, there are some scary dogs on long ropes ... that come lunging.) The beaver dam is interesting to see, but there is no way to continue on the towpath at that point.

It turns out that the Mamakating O&W rail trail also has an entrance right on McDonald Rd. We chose to ride that back to Wurtsboro. There is a supposed continuation of Mamakating that heads northeast (the satellite view shows it), and it might be possible to jump back onto the D&H trail on the other side of the beaver dam blockage. But the official listing for Mamakating shows that this length is not developed ... so we decided not to chance it.

The Mamakating trail back to Wurtsboro is a straight shot ... no problems. That unintended shorter loop was maybe 3 miles total. But worth it!!

Wallkill Valley Rail Trail

great ride!

July, 2025 by v65xtm2gzt

Great ride through the shawingunk mountains ! Trail was great bikes were awesome ! What a beautiful day !!

D&H Rail Trail

I've ridden the trail from Simpson to Buck's Falls which is outside of Starrucca. The trail is well groomed until you hit the other side of Ararat. Then you run into ballast stone and coal silt. No ballast stone or coal silt from Simpson to Ararat.

July, 2025 by seamusmc1950

I've ridden the trail from Simpson to Buck's Falls which is outside of Starrucca. The trail is well groomed until you hit the other side of Ararat. Then you run into ballast stone and coal silt. No ballast stone or coal silt from Simpson to Ararat.

O&W Rail Trail (Ulster County)

a little rough in spots but all in all a great ride !!!

July, 2025 by v65xtm2gzt

Rough in spots but really nice ride !!! Would do it again ! Tough around the steep hill x2 , Tressel bridge !!! But nice scenery and cool breeze Pat and Kevin B

Sullivan O&W Rail Trail

awesome ride

July, 2025 by v65xtm2gzt

Throughly enjoyed the trail end of the trail needs some work otherwise an awesome ride !!!

Wallkill Valley Rail Trail

nicest crushed stone trail ever

June, 2025 by vbergerg_tl

Section from New Paltz (and maybe a mile or two below, I haven’t checked) to a mile or so north of the Rosendale Trestle is superb. Just after the Women’s Studio Workshop is an interesting historical furnace chimney. But then the trail comes apart - chunky gravel and hills I wouldn’t want to come down, leading to Williams Lake (saw lots of landscaping going on but no one using that end of it recreationally). I returned to the Women’s Studiovia the road.

D&H Rail Trail

I have ridden from Lansboro to Steven's Point several times. I'm from the area and can't find the trail from Steven's Point to Starucca. Where can I pick up the trail to Starucca.

June, 2025 by srinker58

I have ridden from Lansboro to Steven's Point several times. I'm from the area and can't find the trail from Steven's Point to Starucca. Where can I pick up the trail to Starucca.

Joseph M. McDade Recreational Trail

has potential to one of the best trails in mid Atlantic

May, 2025 by edmunter

Parts of this trail are incredible. You feel like an early pioneer venturing out beyond the frontier. You are stunned by the natural beauty of the Delaware river. You imagine the grinding of receding glaciers that carved this beauty. You hear the echos of an earlier time. The forest is dense, lush and alive. Groundhogs greet you. Birdsong awaits you. Locals are friendly However parts are hellish if you’re attempting to bike it. Even hiking the bike is dicey and dangerous. Our ortlieb saddle bags fell into the Delaware river at one point. We managed to fish them out by some kind of aquatic miracle It’s also full of Lyme disease carrying ticks so watch out The trail need a make over Any billionaires out there who have a spare penny to repair it, please help!

D & H Canal & Gravity Railroad Heritage Corridor - Port Jervis Branch Trail

D&H

May, 2025 by kaiser

Not a bad ride if you are already riding in the area , not much to see and very short .Not to far up is Port Jervis watershed park area several miles of paved road leading to a look out out the city of Port and various off path trails ( rough terrain )

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Accordion

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