Kingston, NY Running Trails and Maps

597 Reviews

Looking for the best Running trails around Kingston?

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

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Activities
Length
Surfaces
Type
39 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

Billings Trail

3.3 mi
State: CT
Dirt

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Briarcliff-Peekskill Trailway

12 mi
State: NY
Asphalt, Dirt, Grass

Catskill Scenic Trail

26 mi
State: NY
Cinder, Crushed Stone, Dirt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

D & H Canal Linear Park

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

D & H Canal Park

0.6 mi
State: NY
Crushed Stone

D & H Canal Trail - Bashakill Wildlife Management Area

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

Harlem Valley Rail Trail

17.2 mi
State: NY
Asphalt, Crushed Stone

Heritage Trail (NY)

15.1 mi
State: NY
Asphalt, Crushed Stone, Dirt

Hudson Valley Rail Trail

7.1 mi
State: NY
Asphalt

Jones Point Path

2 mi
State: NY
Ballast, Dirt

Kaaterskill Rail Trail

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

Kennedy Trail

1.7 mi
State: NY
Cinder

Kingston Point Rail Trail

1.2 mi
State: NY
Asphalt

Klara Sauer Trail

1 mi
State: NY
Crushed Stone
Accordion

Kress Family Trail

3.1 mi
State: CT
Dirt

Liberty Rail Trail

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

Maybrook Trailway

3.7 mi
State: NY
Asphalt

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

North County Trailway

20.7 mi
State: NY
Asphalt

O&W Rail Trail

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

Old Croton Aqueduct Trail

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

Old Mine Railroad Trail

2.2 mi
State: NY
Dirt

Parksville Rail Trail

3.2 mi
State: NY
Cinder

Putnam Trailway

11.9 mi
State: NY
Asphalt

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

River-to-Ridge Trail

4.9 mi
State: NY
Gravel

Sue Grossman Still River Greenway

2.9 mi
State: CT
Asphalt

Timp-Torne Trail

5.4 mi
State: NY
Dirt

Walden-Wallkill Rail Trail

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

Walkway Over The Hudson

1.6 mi
State: NY
Concrete

Wallkill Valley Rail Trail

21.3 mi
State: NY
Asphalt, Cinder, Dirt, Gravel
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 9 mi Asphalt
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 stunner. The paved pathway begins in Olivebridge, a hamlet in southeastern New York, and spans just shy...
NY 2.7 mi Asphalt
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
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
CT 1.8 mi Asphalt
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. The trail is built on land...
NY 12 mi Asphalt, Dirt, Grass
The Catskill Scenic Trail lives up to its name as it winds through a broad farming valley and small towns in New York's Catskill Mountains. The West Branch of the Delaware River is often in sight,...
NY 26 mi Cinder, Crushed Stone, Dirt
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 Delaware & Hudson Canal Linear Park is 45 acres with a trail situated along the historic D&H Canal. Remains of the original locks, dry dock and waste weirs are visible from the towpath trail....
NY 4.7 mi Ballast, Cinder, Dirt, Grass, 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 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
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
NY 17.2 mi Asphalt, 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 15.1 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 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 Ballast, Dirt
The Kaaterskill Rail Trail offers a beautiful wooded walk 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 Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
NY 1.7 mi Cinder
The Kingston Point Rail Trail will be a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High School,...
NY 1.2 mi Asphalt
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
Accordion
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 Liberty Rail Trail extends about 2.5 miles through the village of Liberty, NY, between Chestnut Street/SR 52 (near West Street) and the old rail trestle in Ferndale. The trail occupies a portion...
NY 2.6 mi Asphalt, Cinder, Dirt, Grass, Gravel
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...
NY 3.7 mi Asphalt
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 former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...
NY 20.7 mi Asphalt
The O&W Rail Trail provides a glimpse into the area’s history from the perspectives of both a historical canal and a railroad. The Delaware & Hudson (D&H) Canal carried coal from Honesdale,...
NY 25.9 mi Asphalt, Cinder, Crushed Stone, Dirt, Grass
At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees and...
NY 26.5 mi Crushed Stone, 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
This rustic unpaved trail, just over three miles in length, runs along a route formerly used by the New York, Ontario, & Western Railway's Main Line through Parksville in Sullivan County, NY. The...
NY 3.2 mi Cinder
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
NY 11.9 mi Asphalt
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
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
Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...
CT 2.9 mi Asphalt
For family riding and walking, the Tannersville Bike Path offers a 2.7 mile stretch of graded dirt path starting on Clum Hill Road directly across from Cortina Valley. The opposite end is on Bloomer...
NY 2.7 mi Dirt, Gravel
Just an hour north of New York City, the Timp-Torne Trail offers a scenic hike through Bear Mountain and Harriman State Parks with panoramic vistas of the Hudson River. The rugged blue-blazed trail...
NY 5.4 mi Dirt
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 Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at just over 1.6 miles—emerges from the trees and over the rooftops of the old riverfront town of...
NY 1.6 mi Concrete
While the Wallkill Valley Railroad no longer carries fruits and vegetables from Ulster County to New York City, trail users can still discover small, family-owned farms and farmers markets serving up...
NY 21.3 mi Asphalt, Cinder, Dirt, Gravel
The William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
NY 13.1 mi Asphalt

Now, More Than Ever, Trails Matter!

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Trails by activity

Recent Trail Reviews

Harlem Valley Rail Trail

lovely

April, 2020 by patick93

Beautiful rail trail.

William R. Steinhaus Dutchess Rail Trail

AWESOME RAIL TRAIL

April, 2020 by gjzambetti

A great experience at every level. Exceptional trail with excellent parking/access points. The Poughkeepsie walking bridge is a great bonus.
Simply the best!

Putnam Trailway

great trail

April, 2020 by bjaffin

In very good shape compared to southern county trail. More hills than expected when cycling south from northern entrance. Scenic ride

Accordion

North County Trailway

North County Review

March, 2020 by nikspringer211

Amazing trail. It’s a great full one or two day trek. I did a 30 mile loop in just over 4 hours, which wasn’t very pleasant to endure, but if you gave yourself ~6 hours you could ride the entire trail (just over 20 miles) in one day, assuming you didn’t have to ride back.

Wallkill Valley Rail Trail

New Paltz to Wallkill

March, 2020 by slipsoup

My friends and I recently rode this trail from the Sojourner Truth parking lot in New Paltz to the end in Wallkill, which is 8 miles. The scenery is nice, but not as nice as the New Paltz to Rosendale leg. The surface is mucky so I'd suggest a hybrid or mountain bike. There are a few, not heavily trafficked street crossings.

Hudson Valley Rail Trail

old map

February, 2020 by bobrick45

this trail now goes into the village of New Paltz. two years ago a section was added that went to South Ohioville road to where a diner is (closed the last time I was there). there is a continuation that connects to Wallkill Valley rail trail as part of the Empire State Trail. I plan on checking that out in the next few months. I am pretty sure part of that extension uses some back roads.

Putnam Trailway

Gorgeous Trail

February, 2020 by bikenrun1205

I love this trail. Well maintained. Very scenic. While hilly, I would say that the hills are not a problem for someone who cycles on a regular basis.

Ashokan Rail Trail

Boiceville trailhead

January, 2020 by rosey123

The Boiceville trailhead is beautiful however the parking lot is too small

William R. Steinhaus Dutchess Rail Trail

Walk on Sunday

November, 2019 by rose.burrus

Great trail for biking and just walking. So nicely maintained!

Wallkill Valley Rail Trail

Started in New Paltz

October, 2019 by michaelberlin66

What a nice ride. If your not use to gravel trails your going to be bounced around a bit but overall it is a great ride. Had a nice snack and glass of wine when we got back to where we started.

Heritage Trail (NY)

great trail

October, 2019 by dirtp1

I have biked about two-thirds of this trail, and it's great. There are several access points, and many places where you can exit the trail to ride on local roads.

Harlem Valley Rail Trail

trail ends in Millerton

October, 2019 by peas67_tl

Beautiful and no crowded from Amenia to Milerton - 8 plus miles from the parking lot indicated on the map. Trail ends in Millerton - I did not ride along rite 22 to pick up the rail trail again for the final five r so miles, as it is crazy town to ride on Route 22. Overall, a pleasant there and back (I went past the parking lot to make a twenty mile ride). I hope that the trail does get connected and soon.

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