Kingston, NY Walking Trails and Maps

871 Reviews

Looking for the best Walking trails around Kingston?

Find the top rated walking trails in Kingston, 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
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Type
50 Results
Activities
Length
Surfaces
Type

Albany-Hudson Electric Trail

36 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

23.8 mi
State: NY
Asphalt, Crushed Stone

Heritage Trail (NY)

19.4 mi
State: NY
Asphalt, Crushed Stone, Dirt

Hudson Valley Rail Trail

7.1 mi
State: NY
Asphalt

Kennedy Trail

1.7 mi
State: NY
Cinder

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

12 mi
State: NY
Asphalt

River-to-Ridge Trail

4.9 mi
State: NY
Gravel

Sue Grossman Still River Greenway

3.4 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
Accordion

Walkway Over The Hudson

1.6 mi
State: NY
Concrete

Wallkill Valley Rail Trail

21.3 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

Jones Point Path

2 mi
State: NY
Asphalt

Kaaterskill Rail Trail

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

Kingston Point Rail Trail

2.15 mi
State: NY
Asphalt

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

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

Klara Sauer Trail

1 mi
State: NY
Crushed Stone

Marcus J. Molinaro Northside Line

0.57 mi
State: NY
Asphalt

Midtown Linear Park

0.9 mi
State: NY
Asphalt

Mohansic Trailway

1 mi
State: NY
Boardwalk, Dirt, Gravel

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel
Trail Image Trail Name States Length Surface Rating
Overview 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...
NY 9 mi Asphalt
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. The electric trolley ran for 30...
NY 36 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
Overview 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...
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
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 23.8 mi Asphalt, Crushed Stone
Overview 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...
NY 19.4 mi Asphalt, Crushed Stone, Dirt
Overview 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...
NY 7.1 mi Asphalt
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers.  The cinder trail, built on a former rail bed,...
NY 1.7 mi Cinder
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
Closure Notice: Due to flooding and storm damage, the Maybrook Trailway from Green Haven Rd. to Depot Hill Rd. See Empire State Trail for more current information. Overview The Maybrook Trailway...
NY 28.6 mi Asphalt
Overview 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...
NY 20.7 mi Asphalt
Overview 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...
NY 1.3 mi Cinder
Overview  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,...
NY 12 mi Asphalt
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
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 2.7 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
Accordion
The Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of Poughkeepsie,...
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 Dutchess County executive who championed it—is a treasure in New York's Hudson Valley region. The 13.1-mile trail runs through what seems...
NY 13.1 mi Asphalt
Overview  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...
NY 26 mi Cinder, Crushed Stone, Dirt, Gravel
Overview 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...
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
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
Overview 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...
NY 2.15 mi Asphalt
Overview 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
Overview 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...
NY 18 mi Asphalt, Cinder, Crushed Stone, Dirt, Grass
Overview 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...
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. The trail is built on land...
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
Overview 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
Overview 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 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
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
The Marcus J. Molinaro Northside Line is a 0.57 mile dual-track trail that connects trail users between the city and town of Poughkeepsie. While the northern end of the route is still under...
NY 0.57 mi Asphalt
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
The Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
NY 1 mi Boardwalk, Dirt, Gravel
Overview 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...
NY 20.65 mi Asphalt, Grass, Gravel
Meandering along the Hudson River, this trail is part of the 51-mile Westchester RiverWalk. Running north from Croton Point Park and through Croton Landing Park, the paved 2.3-mile path offers scenic...
NY 2.3 mi Asphalt

Recent Trail Reviews

Maybrook Trailway

Incredible Trail -- Almost impassable in Dutchess County Right Now

July, 2024 by dryaun

The Dutchess County portion of this incredible biking trail is almost unusable right now. Weeds wildly overgrown and sticking out 4-5 feet into the trail on either side. The Dutchess County people responsible for this negligence should be ashamed of themselves.

Ashokan Rail Trail

Enchanting Views

July, 2024 by wrogers1

While short at 11 miles one way, this trail has a lot to offer. The view of the reservoir with the green Catskill Mountains in the distance is quite enchanting. Much of the ride is through the woods with plenty of shade. The surface is packed cinders and the ride is generally flat. There are plenty of port-a-potties at the trail heads. This is our second time on the trail, so we did view it as worth returning too. Our first trip, during a summer weekend, was quite busy. This time we were there on a rainy weekday in June, and there were minimal people.
We extended the ride by travelling an additional 20 miles on the rode to ride around the reservoir. Starting at the Woodstock Dike Trailhead, we headed east on a very busy Route 28, but only for less than a quarter mile. The rest of the trip had minimal traffic, although I should note it was a rainy weekday. I ‘m unsure how different it would be on a sunny weekend.
We then followed Basin Road to Dike Road where we enjoyed amazing views. Dike Road is on what I believe is the dam at the east end of the Reservoir, offering unobstructed views of the water. From there, we continued on Route 28A. We were a short distance from the Promenade when we encountered a rain storm approaching in from the west. We turned back, managing to get to the car right before the rain began. In total the trip covered 40 miles on hybrid bikes.
While we did not reach the Promenade on this trip, I would highly recommend visiting it. During a previous visit, we took a short drive from the Rail Trail to the Promenade. It was well worth the hassle of loading and unloading the bikes on the car. You will find gorgeous views of the revisor with the mountains in the distance. We even spotted a bald eagle soaring over the water.
It takes us 2.5 hours to drive from our home to the western trailhead. The journey is well worth it. We definitely will be visiting again.

Heritage Trail (NY)

Heritage trail

July, 2024 by flywithme_tl

A great ride . A watch for when you’re in Goshen , if coming from Harriman when you get to where it says end of trail in Goshen proceed straight across into parking lot continue on railroad ave make left on west main then take west main until you see a cemetery on the left then make a right onto a paved walkway near the dead end street then make left to continue on the trail . I am writing this to help others poor signage

Accordion

William R. Steinhaus Dutchess Rail Trail

great ride William trail

July, 2024 by flywithme_tl

Can’t say enough well maintained , a must do !

Walkway Over The Hudson

walkway over Hudson

July, 2024 by flywithme_tl

Great a must do . Food & drinks along with bathrooms on each end of bridge .

Hudson Valley Rail Trail

perfect

July, 2024 by flywithme_tl

Great trail well maintained would be good if porta John was available in the parking lot across from Lowe’s . Plenty of places to get a drink .

Hudson Valley Rail Trail

Beautiful

July, 2024 by jhqr_stone

Beautifully maintained. Started at Walkway over the Hudson rode to new Paltz and back. Super hot day but trail had a lot of shade. We definitely want to explore more of this area

Briarcliff-Peekskill Trailway

Briarcliff-Peekskill trail

July, 2024 by joseph.avdek

I entered the trail on Ryder Road in Ossining and ran to the Teatown preserve and back (approximately 6 miles).

The trail is overgrown and not well maintained. There are points that are severely sloped and there are rocks hidden in high grass. Along the trail there is a creak that has stagnant water. The high grass and water leads to a large amount of bugs. I found a tick on my leg after the run.

On the trail there are abrupt up-hills that are not maintained or easy to traverse without coming to a slow walk due to rocks and roots. The scenery is beautiful but the trail needs a lot of love and care.


Maybrook Trailway

beautiful trail with an ownership dispute

July, 2024 by vbergerg_tl

Beautiful needed trail, extending the Dutchess Trail down to Brewster. Pity there seems to be some big ownership/maintenance dispute going on I guess between Dutchess County and NYS? Because right now no one is cutting back the weeds on the Dutchess County side and there’s a big defensively toned sign up saying that Dutchess County is not responsible.

Sue Grossman Still River Greenway

B bear aware

July, 2024 by willthegreat

Twice this week I saw a bear x the trail near the USA transfer station.
Also saw two women digging up poppies! That's a no no!
The extended trail that ends by the motor vehicle bldg has beautiful poppies and other ornamentals! Well done you guys!

Basha Kill Rail Trail (Shawangunk Ridge Trail/Long Path)

Overgrown, snakes and hard to navigate

June, 2024 by allison22600

Snakes, bugs, overgrown, not maintained, trail ends, unmarked, Waste of time!

Heritage Trail (NY)

Heritage trail

June, 2024 by flywithme_tl

A must ride stopped in Middletown for a bite to eat .

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Accordion

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