Roscoe, NY Walking Trails and Maps

561 Reviews

Looking for the best Walking trails around Roscoe?

Find the top rated walking trails in Roscoe, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
33 Results
Activities
Length
Surfaces
Type

Andes Rail Trail

4 mi
State: NY
Dirt, Grass

Ashokan Rail Trail

11.5 mi
State: NY
Crushed Stone

Ashokan Reservoir Promenade

2.7 mi
State: NY
Asphalt

D & H Canal Towpath

0.4 mi
State: NY
Crushed Stone

Heritage Trail (NY)

19.4 mi
State: NY
Asphalt, Crushed Stone, Dirt

Hudson Valley Rail Trail

7.1 mi
State: NY
Asphalt

Parksville Rail Trail

1.3 mi
State: NY
Cinder

Walden-Wallkill Rail Trail

4.3 mi
State: NY
Asphalt, Ballast, Cinder, Crushed Stone, Dirt, Grass, Gravel

Wallkill Valley Rail Trail

21.4 mi
State: NY
Asphalt, Cinder, Dirt, Gravel

Catskill Scenic Trail

26 mi
State: NY
Cinder, Crushed Stone, Dirt, Gravel

D & H Canal Linear Park and Towpath Trail

6.84 mi
State: NY
Ballast, Cinder, Dirt, Grass, Gravel

D & H Canal Trail - Bashakill Wildlife Management Area

5.7 mi
State: NY
Ballast, Cinder, Dirt, Grass

D&H Rail Trail

39 mi
State: PA
Ballast, Cinder, Crushed Stone, Dirt

Joseph M. McDade Recreational Trail

31.2 mi
State: PA
Gravel

Kaaterskill Rail Trail

2 mi
State: NY
Concrete, Dirt, Grass, Gravel

Kingston Point Rail Trail

2.15 mi
State: NY
Asphalt

Lackawanna River Heritage Trail

17.9 mi
State: PA
Asphalt, Crushed Stone

Mamakating Rail Trail

3.2 mi
State: NY
Ballast, Cinder, Grass, Gravel

O&W Rail Trail (Ulster County)

18 mi
State: NY
Asphalt, Cinder, Crushed Stone, Dirt, Grass
Accordion

River-to-Ridge Trail

4.9 mi
State: NY
Gravel

D & H Canal Park

0.6 mi
State: NY
Crushed Stone

Endless Mountains Trail

9.2 mi
State: PA
Ballast, Dirt

Liberty Rail Trail

2.4 mi
State: NY
Asphalt, Cinder, Dirt, Grass, Gravel

O&W Trail (PA)

32 mi
State: PA
Dirt, Gravel

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel

Hudson River Brickyard Trail

1.5 mi
State: NY
Asphalt, Woodchips

Hunter Branch Rail Trail

1.5 mi
State: NY
Boardwalk, Crushed Stone, Dirt, Grass

Hunter Regional Trail

6.1 mi
State: NY
Boardwalk, Concrete, Crushed Stone, Dirt, Grass, Gravel

Liberty Loop Trail

2.5 mi
State: NJ
Crushed Stone, Dirt, Grass, Gravel

Midtown Linear Park

0.9 mi
State: NY
Asphalt
Trail Image Trail Name States Length Surface Rating
The Andes Rail Trail begins in the quaint town of Andes in the beautiful Catskill Mountains region of southeastern New York and follows a branch of the former Delaware and Northern Railroad. At the...
NY 4 mi Dirt, Grass
The Ashokan Rail Trail is an 11.5-mile multi-use trail that traces the northern edge of the Ashokan Reservoir, which provides a large proportion of New York City's drinking water. The trail sits on...
NY 11.5 mi Crushed Stone
With vistas of the Catskill Mountains and a vast blue lake, the Ashokan Reservoir Promenade is a paved pathway that spans just shy of 3 miles along the reservoir's southern shoreline. About the...
NY 2.7 mi Asphalt
Although the D & H Canal Towpath is a short pathway (about 1 mile roundtrip), it offers scenic views of the Delaware and Hudson Canal and the Delaware River in Minisink Ford, New York. You’ll see the...
NY 0.4 mi Crushed Stone
Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
NY 19.4 mi Asphalt, Crushed Stone, Dirt
Offering a picturesque and family-friendly adventure, the Hudson Valley Rail Trail stretches 7.1 miles through hardwood forests, over Black Creek, and under two spectacular stone-arch bridges....
NY 7.1 mi Asphalt
The Parksville Rail Trail is the northernmost section of the Sullivan O&W Trail, which runs for 20.65 miles in Sullivan County in 7 distinct sections along the previous O&W Railroad Main Line and Port...
NY 1.3 mi Cinder
For family riding and walking, the Tannersville Bike Path offers a 2-mile stretch of graded dirt path starting on Clum Hill Road directly across from Cortina Valley. The opposite end is on Bloomer...
NY 2 mi Dirt, Gravel
The Walden-Wallkill Rail Trail is built on a former Conrail right-of-way. Conrail and its predecessors, Penn Central, New York Central, and The Wallkill Valley Railway, provided service to farmers...
NY 4.3 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt, Grass, Gravel
The Wallkill Valley Rail Trail runs 21.4 miles between Kingston and Gardiner through woods, fields, farmland. About the Route The corridor’s current incarnation as a linear park welcomes all...
NY 21.4 mi Asphalt, Cinder, Dirt, Gravel
The Catskill Scenic Trails runs for 25.6 miles between Bloomville and Roxbury, winding through a broad farming valley and small towns in New York’s Catskill Mountains. The West Branch of the Delaware...
NY 26 mi Cinder, Crushed Stone, Dirt, Gravel
The D&H Canal Linear Park and Towpath Trail, situated in Wurtsboro, NY carries trail users for 6.84 miles along the former towpath for the historic Delaware and Hudson Trail. Use of motorized...
NY 6.84 mi Ballast, Cinder, Dirt, Grass, Gravel
The Bashakill Wildlife Management Area is located on the Orange County-Sullivan County border just south of Wurtsboro, New York. It consists of over 3,000 acres of wetlands and uplands which were...
NY 5.7 mi Ballast, Cinder, Dirt, Grass
In the forested and farm-dotted hills of Pennsylvania’s northeastern corner, the D&H trail runs 39 miles between the small town of Simpson and the state’s northern border. The crown jewel of the...
PA 39 mi Ballast, Cinder, Crushed Stone, Dirt
Note: With a surface of large-sized gravel, the trail is not recommended for road bikes or mountain bikes with no suspension.  The Joseph M. McDade Recreational Trail runs nearly the length of the...
PA 31.2 mi Gravel
The Kaaterskill Rail Trail offers a beautiful, wooded route through Haines Falls in eastern New York, nestled in the northern Catskills. It begins at the historical Ulster & Delaware Train Station,...
NY 2 mi Concrete, Dirt, Grass, Gravel
The Kingston Point Rail Trail is a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High School, City...
NY 2.15 mi Asphalt
The multi-use Lackawanna River Heritage Trail (LRHT) follows Pennsylvania's Lackawanna River and, when complete, will be more than 70 miles. The trail begins at the confluence of the Lackawanna and...
PA 17.9 mi Asphalt, Crushed Stone
The Mamakating Rail Trail is part of the Sullivan O&W Trail, which runs for 20.65 miles in Sullivan County in 7 distinct sections along the previous O&W Railroad Main Line and Port Jervis...
NY 3.2 mi Ballast, Cinder, Grass, Gravel
The O&W Rail Trail follows the route of the old NY O&W Railroad (Kingston-Port Jervis Branch) right-of-way for 19.1 miles through Ulster County, NY, between Kingston and Ellenville. The O&W Rail...
NY 18 mi Asphalt, Cinder, Crushed Stone, Dirt, Grass
Accordion
Connecting the Walkill River and Shawangunk Ridge, the aptly named River-to-Ridge Trail, which opened in September 2018, runs from New Paltz to the Mohonk Preserve. Begin at the Carmine Liberta Bridge...
NY 4.9 mi Gravel
The City of Port Jervis is the latest community to save a portion of the former D&H Canal and turn it into a greenway for use by residents and visitors. A section of the canal, which is approximately...
NY 1 mi Cinder, Gravel
The D & H Canal towpath is nestled within the 300-acre D & H Canal Park in the New York hamlet of Cuddebackville. The crushed-stone trail, stretching just over a half mile, is one section of a larger...
NY 0.6 mi Crushed Stone
The local riding club enjoyed this former rail line, which was purchased in 1944 for a dollar from the Delaware, Lackawanna & Western Railroad, as a bridle trail for many years. It changed management...
PA 9.2 mi Ballast, Dirt
The Liberty Rail Trail is part of the Sullivan O&W Trail, which runs for 20.65 miles in Sullivan County in 7 distinct sections along the previous O&W Railroad Main Line and Port Jervis...
NY 2.4 mi Asphalt, Cinder, Dirt, Grass, Gravel
The O&W Trail (PA) stretches 32 miles throughout northeastern Pennsylvania. About the Route There are two trails named the O&W: one in New York and this one in Pennsylvania. Although the...
PA 32 mi Dirt, Gravel
The Sullivan O&W Trail runs for 20.65 miles in Sullivan County in 7 distinct sections along the NY O&W Railroad Main Line and Port Jervis-Kingston Branch rights-of-way. The Sullivan O&W Rail Trail...
NY 20.65 mi Asphalt, Grass, Gravel
The Basha Kill Rail Trail is part of the Sullivan O&W Trail, which runs for 20.65 miles in Sullivan County in 7 distinct sections along the previous O&W Railroad Main Line and Port Jervis...
NY 5.5 mi Dirt, Grass
The Hudson River Brickyard Trail runs 1.5 miles from North Street to John Street in East Kingston. Located in Sojourner Truth State Park, the trail follows the shoreline and offers scenic views of...
NY 1.5 mi Asphalt, Woodchips
The Hunter Branch Rail Trail (HBRT) is a recently completed segment of the Hunter Regional Trail (HRT), a network of rail-trails that run along a former railroad corridor in the Town of Hunter,...
NY 1.5 mi Boardwalk, Crushed Stone, Dirt, Grass
The Hunter Regional Trail (HRT) is a network of rail-trails that run along a former railroad corridor in Hunter, NY. Currently, there are 6.1 miles of open trail in the hamlet of Haines Falls, the...
NY 6.1 mi Boardwalk, Concrete, Crushed Stone, Dirt, Grass, Gravel
Located in the Wallkill River National Wildlife Refuge, the Liberty Loop Trail is 2.5 miles long with a surface of gravel, grass, dirt, and crushed stone. Some portions may have raised wooden planks...
NJ 2.5 mi Crushed Stone, Dirt, Grass, Gravel
Following the former Ulster & Delaware Railroad (U&D) corridor, the Midtown Linear Park is part of the Kingston Greenline. Running through Midtown between Westbrook Lane and Cornell Street, the ADA...
NY 0.9 mi Asphalt

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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