Kingston, NY Cross Country Skiing Trails and Maps

931 Reviews

Looking for the best Cross Country Skiing trails around Kingston?

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

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Activities
Length
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Type
36 Results
Activities
Length
Surfaces
Type

Albany County Helderberg-Hudson Rail Trail

8.9 mi
State: NY
Asphalt, Crushed Stone

Albany-Hudson Electric Trail

26.6 mi
State: NY
Asphalt, Crushed Stone

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

Harlem Valley Rail Trail

26.4 mi
State: NY
Asphalt

Heritage Trail (NY)

19.4 mi
State: NY
Asphalt, Crushed Stone, Dirt

Kress Family Trail

3.1 mi
State: CT
Dirt

Litchfield Community Greenway

2.5 mi
State: CT
Boardwalk, Crushed Stone, Dirt

Maybrook Trailway

28.6 mi
State: NY
Asphalt

North County Trailway

20.7 mi
State: NY
Asphalt

Parksville Rail Trail

1.3 mi
State: NY
Cinder

Putnam Trailway

11.8 mi
State: NY
Asphalt

Sue Grossman Still River Greenway

3.4 mi
State: CT
Asphalt

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
Accordion

Jones Point Path

2 mi
State: NY
Asphalt

Kaaterskill Rail Trail

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

Mamakating Rail Trail

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

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

O&W Rail Trail (Ulster County)

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

Old Croton Aqueduct Trail

26.5 mi
State: NY
Crushed Stone, Dirt, Grass, Gravel

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Briarcliff-Peekskill Trailway

12 mi
State: NY
Asphalt, Dirt, Grass

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

D & H Canal Park

0.6 mi
State: NY
Crushed Stone

Liberty Rail Trail

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

Old Mine Railroad Trail

2.2 mi
State: NY
Dirt

Billings Trail

3.3 mi
State: CT
Dirt

Hunter Regional Trail

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

Klara Sauer Trail

1 mi
State: NY
Crushed Stone
Trail Image Trail Name States Length Surface Rating
Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis and community connector for residents living southwest of...
NY 8.9 mi Asphalt, Crushed Stone
The Albany-Hudson Electric Trail (AHET) follows a 36-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. There are several gaps along...
NY 26.6 mi Asphalt, Crushed Stone
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
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful 26.2-mile wooded pathway along the former New York & Harlem Railroad...
NY 26.4 mi Asphalt
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
The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
CT 3.1 mi Dirt
The Litchfield Community Greenway runs along the former Shepaug Railway railbed in the Town of Litchfield. Operational from 1878 to 1948, the railroad line ran between between Litchfield and...
CT 2.5 mi Boardwalk, Crushed Stone, Dirt
The Maybrook Trailway is a paved multi-use trail stretching across Putnam and Dutchess counties in New York state. The trail, which is owned and was built by Metro North Rail, occupies the former...
NY 28.6 mi Asphalt
At just over 20 miles, the North County Trailway is the longest of four rail trails created from the former New York Central Railroad’s Putnam Division line. The trail travels through communities in...
NY 20.7 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
The old New York Central rail line that ran from the Bronx to communities north of the city in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends, tourists...
NY 11.8 mi Asphalt
Just over 3 miles long, the Sue Grossman Still River Greenway is anchored by Winsted to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck Division of the New York,...
CT 3.4 mi Asphalt
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
Accordion
The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
NY 2 mi Asphalt
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 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 first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
CT 5 mi Asphalt, Crushed Stone, Dirt
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
The Old Croton Aqueduct Trail spans 26.5 miles across West Chester County, NY. It is often a singletrack dirt pathway that winds through communities and trees and provides an oasis of green just north...
NY 26.5 mi Crushed Stone, Dirt, Grass, Gravel
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, Dirt, Grass
The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill.  About the Route The trailway...
NY 12 mi Asphalt, Dirt, Grass
The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...
NY 3.8 mi Dirt
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 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
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
NY 2.2 mi Dirt
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
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
CT 3.3 mi Dirt
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
The Klara Sauer Trail (formerly known as the Beacon Riverside Trail) runs for 1 mile along the Hudson River on the west side of New York's village of Beacon. The trail occupies the same corridor as...
NY 1 mi Crushed Stone

Recent Trail Reviews

Maybrook Trailway

WARNING !!!!! - TREES DOWN EVERYWHERE For 3 Mile Stretch

July, 2026 by sisophous

The trail is not accessible for a 3-mile stretch. From Green Haven and then Eastbound is impossible to pass. Trees have fallen down virtually every 50 yards blocking passage. I carried my bike past about 6 trees and each time I saw another tree blocking the trail. I came across a clean up crew that told me the downed trees went all the way to Green Haven. I was 3 miles east of Green Haven when the mess started. There is also debris along the entire section which I was fortunate not to get a flat tire. The cleaning crew told me they have only 4 people and they will try to hire a contractor to clear the trees. There is no way a crew of 4 people could handle this. It would take them months to clean it up. (July 10, 2026)

Ashokan Rail Trail

Gravel, Not for skinny tires, but otherwise great

July, 2026 by golisa

I disagree with the description that this trail is packed enough for skinny road tires. There are parts with thicker gravel and I was glad to have gravel tires on my bike and even then it was a bumpy ride. Nice scenery, not too crowded, good bathrooms. Overall loved it.

Maybrook Trailway

Brewster Trailway Bridge and CT State Line and more

July, 2026 by normrtt

The Trailways Bridge over the river in Brewster is open, eliminating the on-road detour. The eastern end is currently at the NY/CT line at Farrington Woods (with trail parking) in CT. Long range plans are to develop the CT portion of the RR path to Danbury.
There are far more legit parking areas than currently shown on TrailLink. Services are few and some might seem close lack easy access from route to road. High point is Whaley Lake. The trail is in good condition for it's entire length.

Accordion

Ashokan Rail Trail

Quiet, peaceful, looking for a different perspective in life, these trails will definitely will. The Red trail leads to the science parts of the Hudson. The blue trail goes all around the large pond which is also beautiful.

May, 2026 by z4fold01

Quiet, peaceful, looking for a different perspective in life, these trails will definitely will. The Red trail leads to the science parts of the Hudson. The blue trail goes all around the large pond which is also beautiful.

Ashokan Rail Trail

Views, History and nice bike path

December, 2025 by tombegg14

IT had great views, history and parking. Stopped and had our lunch in a quiet spot overlooking the water. Saw a Bear ¿ at one end..he didn’t catch us :)

Ashokan Rail Trail

One of our East coast favorites

November, 2025 by kleistikow

We biked on a Sunday in May. Plenty of parking at West Hurley. The scenery was stunning and varied. Started in forests, with some reminders of people who made their living in these woods. Ended with views of Catskills and the reservoir. Truly stunning views, wide, well maintained trail that we cycled on our hybrids.

North County Trailway

Smooth riding, lovely view- part 2

November, 2025 by kleistikow

The ‘protected bike lane’ is more like a highway breakdown lane, but separated by a guardrail. Again, not pretty, but it is a safe and efficient way to get from Point A to Point B.

North County Trailway

Smooth riding, lovely views

November, 2025 by kleistikow

We parked at northern end of South County trail, Elmsford, and turned around at mile 33 marker, Shenorock. Paved trail is perfectly maintained, beautiful foliage. The next time we would park at New Castle, however, to avoid rush hour traffic smells and sounds of Saw Mill River Parkway and Route 87. Both are quite close to trail. The Elmsford-New Castle section also has portions where trail leaves woods and is essentially in protected bike lane along county roads. Not pleasant ruding, although certsinly efficient wat you bike from Point A to Point B. These trails are seamlessly connected, leafing to MYC.

Naugatuck River Greenway

Naugatuck River Greenway-Torrington CT Section(s)

October, 2025 by marieperriello86

Currently there is a couple of sections that are really nice for the work thats been completed, but will be a fantastic trail once they have completed the sections necessary to connect them into one long trail. All the sections completed are mostly all paved and are great for walking/jogging/biking & wheelchair/stroller friendly. The only exception is tgr Naugatuck River Greenway section that starts at the Sullivan Senior Center, which has a paved trail that runs parallel to the the river and ends at the side road which you continue down a one way street that almost zig zags until you reach palmer bridge. Crossing the bridge and crossing to the paved trail that goes behind a condominium and continues until the end of the dirt parking lots (trail is paved) of John Toro Sports Complex, where the pavement ends towards the actual field. Then it transitions to the field with no defined trail. The Trail at that point isnt really distinct. I lived here most of my life and I didnt know until I saw a news article about The Rainbow Bridge and found that the trail in fact extended past where the pavement ends and continues straight past the dog park past both the first baseball field, the soccer field, and then about halfway through the 2nd baseball field there is a wide opening in the forest, where you then see the entrance to the Rainbow Bridge Trail. Which is an amazing small half looped trail, with some of the most beautiful works of art, and tributes to various pets (photos, stepping stones/memorial rock garden, a memorial fence, k-9 officers memorial bulletin board(s), sculptures, poems, signs, chairs, then the rainbow Bridge which is adorned with photos, momentos, stories, collars & tributes to pets of those who came to place their beloved pets memorials. After you find the exits shortly after that you can see the wide open pathway continues for a while on but ends at a fenced off area that currently is a business/underutilized "Sports park" that will eventually be replaced with a connector trail that will connect with other nearby trails.

Sullivan O&W Rail Trail

roots and railroad ties

October, 2025 by bettysaar

We decided to start across from the winery, and end our trip there. We went one way and hit roots and railroad ties immediately. We turned around and got the same. Needless to say, the winery was great. Would be a perfect hiking trail. It was beautiful.

Heritage Trail (NY)

well maintained , interesting sites, and views along the way.

October, 2025 by toddburrparts

I rode from Harriman to the edge of Goshen. Nice smooth, pavement with little or no bumps. I found some interesting sites and information along the way. I will return to ride the second half of this heritage Trail.

O&W Rail Trail (Ulster County)

O&W Kingston - Kerhonkson

September, 2025 by kaiser

.With a mix of cinders , gravel , dirt & pavement this makes for a nice interesting ride . Along the way in High Falls make a left and visit the D+H canal museum its about a mile down the road . Once you venture a mile and half through a grass area the trail stops however pedal straight out on to Lucas tpk & make left onto 209 then left on main & right on scenic you will then pick up the trail to accord

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Accordion

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