Kingston, NY Horseback Riding Trails and Maps

937 Reviews

Looking for the best Horseback Riding trails around Kingston?

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

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Activities
Length
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Type
11 Results
Activities
Length
Surfaces
Type

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

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

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel
Trail Image Trail Name States Length Surface Rating
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 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 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 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 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

Recent Trail Reviews

D & H Canal Park

Easy

August, 2026 by k80laine

Cute park area, playground for kids, pavilion, picnic tables, grills. Boat launch and museum, although the museum had a sign that it is no longer open. I parked at the visitor center and biked the Heritage Trail. Easy, gravel, a couple of ponds along the way. Ends at 209.

Sue Grossman Still River Greenway

first time biking!

August, 2026 by 6twms57vv9

Hubby & I went this morning for a trial run with my new e-bike! It was tons of fun!!!!

Ashokan Rail Trail

Beautiful views, well kept and wide trail. Olive to Boiceville has best views. "Road Bikes" are named to be on the road.

August, 2026 by liberty100realty

Beautiful views, well kept and wide trail. Olive to Boiceville has best views. "Road Bikes" are named to be on the road.

Accordion

New Milford River Trail

A Little variety. scenic Trail along the river.

July, 2026 by toddburrparts

Mostly cinder. Started from access lot off of RT 7. Shared RT Trail with the Town Of new Milford. Parallels an active track. Good variety of terrain and scenery..

Albany-Hudson Electric Trail

Started at Nassau Lake TH

July, 2026 by adsaxs

We are casual cyclists (no ebikes) and decided to take a short ride on this trail. We parked at the Nassau Lake Trailhead which has about 13 parking spots. We headed towards East Greenbush and cycled about 8 miles before turning around. The 8 mile section of the trail we cycled was paved and very well maintained. There was a slight elevation gain in this section but made for a nice downhill on the way back. There were no amenities on the 8 mile route. The trail had a couple of easy street crossings but was mostly off-road.

On the way back, we continued pass the TH parking for about 3 miles to the Village of Nassau to have a look. There is another TH in town next to a small park and across the street from an ice cream shop. This section of the trail in the village was flat. If we had the time, we would have gone further.

I would recommend this trail.

North County Trailway

Now renamed to the Andrew O'Rourke Westchester County Trailway

July, 2026 by joann.brereton

Wonderful trail. Part of the larger Empire State Trailway. This part from Eastview to Baldwin Place is the section I ride the most. Mostly shaded once you're north of Millwood with plenty of spots where you can stop for a bite or veer off for road riding near the reservoirs.

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.

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.

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Accordion

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