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 290 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

Heritage Trail (NY)

Heritage trail update!

December, 2024 by flywithme_tl

Great trail a must do . FYI bridge #1,2,3,4 were under construction but are now complete and the trail is open complete . When in Monroe just before overpass there is a good burger and place called Wayback burger . You have to pedal through a gas station lot but it’s next door .

Wallkill Valley Rail Trail

worth the time & effort

October, 2024 by flywithme_tl

Started 3 miles south of New Paltz & ride all the way to Kingston , plenty of places to eat & drink in New Paltz after that there is a farm brewery on your right going north & a little health food eatery in the middle of nowhere by a campsite on the left going north after that you come to get Rosendsle trestle , the mining caves ( you can feel the cold air mass as you ride by ) Once you get to Kingston you pedal via rroad to the town

River-to-Ridge Trail

no rail trail but doable

October, 2024 by flywithme_tl

Trail is all gravel so be careful ! It starts in the center of town in New Paltz goes into a field of green & a view of a mountain it’s ok but I would not do again .

Accordion

D&H Rail Trail

Some of it is very nice, and some of is VERY rough

September, 2024 by chrisseier

Started in Simpson and headed north. The first 12 miles is very nice, except for the occasional noise from the ATV trail nearby. The next eight miles is a little rough, but not too bad. Then a mile of the trail was very soft, like they were working on the trail. After that, it becomes VERY rough - riding on balast. Some very nice scenery; has the potential to be a great trail - if they ever finish cindering the full length of the trail.

O&W Rail Trail (Ulster County)

O&W Kingston

September, 2024 by flywithme_tl

Nice trail a must do . From Kingston it’s paved at least 5 -6 miles the rest is easy ride great scenery !

Heritage Trail (NY)

A paved gem

August, 2024 by eswnyc

This isn’t the most scenic trail in the world, but it’s in spectacular condition, paved from end to end, busy on weekends but never overcrowded. There are a few nice stops along the trail. Beware: there is a slightly confusing part in Goshen where the trail has a short gap - the signage is not great so you might fumble around to find the next section, but it’s totally worth the trouble.

D & H Canal Linear Park and Towpath Trail

Another disappointing part of the Sullivan County trail network

August, 2024 by eswnyc

Wildly inconsistent and discontinuous trail. Has potential, but I sense it will be many, many years before this will rival the trails on the east side of the Catskills. Skip this and just go to the Heritage Trail in Middletown.

Sullivan O&W Rail Trail

overgrown, unmaintained

August, 2024 by mwoods54321

I tried this trail starting in two spots. First at the north end off 208. The first few hundred yards are good, but then it becomes overgrown. I went through the brush and mud for another few hundred yards, but turned around at a washed out culvert. Next I drove to the north end of the southern section off S road. This was better. Bumpy with roots across the trail. Foot tall grass in most places, but passable for a half mile or so. After the underpass there are several bridges in degrading condition. I didn't dare ride across, but walked these. There were also downed trees in two spots. A little over a mile in I turned around at another rotting bridge that had 3 large snakes (I believe Northern Water Snakes, but not 100% sure).
I wouldn't waste your time with trying this trail.

Heritage Trail (NY)

Heritage Trail a must do again!

August, 2024 by flywithme_tl

Great trail did from Harriman to Middletown plenty of opportunities to get food & water . I recommend Mason’s Place in New Hampton right on the trail breakfast lunch , dinner & bar . Very cool 1866 place , lots of history , good food . The owner Brett was very accommodating and offered to stay late for us .

Heritage Trail (NY)

Trail Maintenance

August, 2024 by shines19

Rode from Harriman ti right before downtown Chester. The trail is closed for maintenance at about the 7 mile marker.

Ashokan Rail Trail

great bike trail

July, 2024 by frednshapiro

This mostly flat, well maintained trail goes though woods and across dykes. The scenery makes this a near perfect trail.

O&W Rail Trail (Ulster County)

Newly paved north end!

July, 2024 by bsmith4_tl

Had a great ride yesterday on the north end going from Kingston trailhead to just before Marbletown wooded trail. Marbletown south was a little muddy from recent rains. Ran into 3 folks on horses there too!

Find Nearby City trails

Accordion

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