Callicoon, NY Bike Trails and Maps

632 Reviews

Looking for the best Bike trails around Callicoon?

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

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Activities
Length
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Type
23 Results
Activities
Length
Surfaces
Type

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

Parksville Rail Trail

1.3 mi
State: NY
Cinder

River-to-Ridge Trail

4.9 mi
State: NY
Gravel

Sussex Branch Trail

21.2 mi
State: NJ
Cinder, Dirt, Grass

Trolley Trail (Lehigh Valley)

4.7 mi
State: PA
Boardwalk, Crushed Stone, Dirt, Grass

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

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

Iroquois Trail

1.8 mi
State: PA
Crushed Stone

Lackawanna River Heritage Trail

17.9 mi
State: PA
Asphalt, Crushed Stone

Luzerne County National Recreation Trail

1.8 mi
State: PA
Cinder, Concrete, Gravel

O&W Rail Trail (Ulster County)

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

Paulinskill Valley Trail

27 mi
State: NJ
Ballast, Cinder, Crushed Stone, Dirt, Grass

D & H Canal Park

0.6 mi
State: NY
Crushed Stone

Liberty Rail Trail

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

O&W Trail (PA)

8 mi
State: PA
Dirt, Gravel

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel
Trail Image Trail Name States Length Surface Rating
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
Overview 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...
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
Closure Notice: The Heritage Trail is closed between Bridge #1 (Leigh Ave., Chester) and Bridge #4 (Craigville Rd., Blooming Grove) through Fall 2024. See Orange County, NY's website for more...
NY 19.4 mi Asphalt, Crushed Stone, Dirt
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
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
Overview The Sussex Branch Trail is a 21.2-mile trail that runs between Branchville and Byram in northern New Jersey. Following a former railroad corridor, the surface of the unpaved trail is a mix...
NJ 21.2 mi Cinder, Dirt, Grass
The Trolley Trail uses a former interurban line to link several communities north of Scranton. The trail comprises two disconnected sections that total 4.7 miles, although the nonprofit Countryside...
PA 4.7 mi Boardwalk, Crushed Stone, Dirt, Grass
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
Overview 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...
NY 21.4 mi Asphalt, Cinder, Dirt, 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 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
Overview    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...
PA 39 mi Ballast, Cinder, Crushed Stone, Dirt
The Iroquois Trail is scenic and remote, stretching about 2 miles through Tunkhannock, a gateway community to the Endless Mountains in northeastern Pennsylvania. The rail-trail follows the route of...
PA 1.8 mi Crushed Stone
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
Tracing nearly two miles of riverfront, the Luzerne County National Recreation Trail (also known as the Luzerne County Rail Trail) will eventually form a 16-mile pathway along an active railway. Chain...
PA 1.8 mi Cinder, Concrete, Gravel
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 Paulinskill Valley Trail follows a creek by the same name through a section of rural New Jersey with a strong German influence. In fact, the word kill is Dutch for “riverbed or stream...
NJ 27 mi Ballast, Cinder, Crushed Stone, Dirt, Grass
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
Accordion
There are two trails named the O&W: one in New York and this one in Pennsylvania. Although the trail stretches 32 miles (as shown on the map), only the first 8 miles of trail (from Simpson to...
PA 8 mi Dirt, Gravel
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
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

Recent Trail Reviews

O&W Rail Trail (Ulster County)

O&W Kingston

September, 2024 by flywithme_tl

Nice trail a must do . From Kingston it’s paved at least 5 -6 miles the rest is easy ride great scenery !

Sussex Branch Trail

Single Track Mountain Bike Kinda Trail

August, 2024 by scott123180

Tried this trail with 35mm's but it's really a mountain biking trail. Single track and a bit overgrown in places. I'm sure other parts of it are nice. I wish it was a bit more maintained and wider.

Heritage Trail (NY)

A paved gem

August, 2024 by eswnyc

This isn’t the most scenic trail in the world, but it’s in spectacular condition, paved from end to end, busy on weekends but never overcrowded. There are a few nice stops along the trail. Beware: there is a slightly confusing part in Goshen where the trail has a short gap - the signage is not great so you might fumble around to find the next section, but it’s totally worth the trouble.

Accordion

D & H Canal Linear Park and Towpath Trail

Another disappointing part of the Sullivan County trail network

August, 2024 by eswnyc

Wildly inconsistent and discontinuous trail. Has potential, but I sense it will be many, many years before this will rival the trails on the east side of the Catskills. Skip this and just go to the Heritage Trail in Middletown.

Sullivan O&W Rail Trail

overgrown, unmaintained

August, 2024 by mwoods54321

I tried this trail starting in two spots. First at the north end off 208. The first few hundred yards are good, but then it becomes overgrown. I went through the brush and mud for another few hundred yards, but turned around at a washed out culvert. Next I drove to the north end of the southern section off S road. This was better. Bumpy with roots across the trail. Foot tall grass in most places, but passable for a half mile or so. After the underpass there are several bridges in degrading condition. I didn't dare ride across, but walked these. There were also downed trees in two spots. A little over a mile in I turned around at another rotting bridge that had 3 large snakes (I believe Northern Water Snakes, but not 100% sure).
I wouldn't waste your time with trying this trail.

Heritage Trail (NY)

Heritage Trail a must do again!

August, 2024 by flywithme_tl

Great trail did from Harriman to Middletown plenty of opportunities to get food & water . I recommend Mason’s Place in New Hampton right on the trail breakfast lunch , dinner & bar . Very cool 1866 place , lots of history , good food . The owner Brett was very accommodating and offered to stay late for us .

Heritage Trail (NY)

Trail Maintenance

August, 2024 by shines19

Rode from Harriman ti right before downtown Chester. The trail is closed for maintenance at about the 7 mile marker.

Ashokan Rail Trail

great bike trail

July, 2024 by frednshapiro

This mostly flat, well maintained trail goes though woods and across dykes. The scenery makes this a near perfect trail.

Paulinskill Valley Trail

Could be so much better

July, 2024 by norsteinberg

Rode from Blairstown to knowlton and back. 14 miles. Goes for a good distance in a tree covered environment which usually is good However, the ground is still wet often, for biking the surfaces vary which is hard enough but when you have to bike through “wagon wheel ruts in the ground”, uncut grass, single file, avoid bushes, etc. not a lot of fun. Was watching the ground so not to slip. But the biggest fault was, there was no signage when the bike trail went on roads and then back on the trail. At least six or 7 times wish they had signs that said turn here, go left. We almost ended up on the runway of the local Blairstown Airport Also, it end before the Pauls Kill Viaduct Which is a major structure in NJ - was the largest concrete structure built in the world when it was built. Does not tell us how to there. Only a quarter a mile further ?? Lastly, in this section enjoy seeing old rail artifacts, country farms etc. not a lot here

O&W Rail Trail (Ulster County)

Newly paved north end!

July, 2024 by bsmith4_tl

Had a great ride yesterday on the north end going from Kingston trailhead to just before Marbletown wooded trail. Marbletown south was a little muddy from recent rains. Ran into 3 folks on horses there too!

Catskill Scenic Trail

Started in Roxbury and fell a couple of miles short of finishing trail but headed back. A lot of mud towards Bloomfield section.Can't say enough about the views. Totally fine for any gravel bike or hybrid .

July, 2024 by antross73

Started in Roxbury and fell a couple of miles short of finishing trail but headed back. A lot of mud towards Bloomfield section.Can't say enough about the views. Totally fine for any gravel bike or hybrid .

Ashokan Rail Trail

Disappointed

July, 2024 by schneidny

My experience did not match the glowing description and reviews for this trail. While I agree it can be ridden with a road bike as I did it makes for a very rough ride. The surface is clearly not crushed stone as advertised but rather gravel with 1/4 to 1/2” pebbles. Furthermore with the exception of a few hundred feet at the beginning (West Hurley) you don’t see the lake, the rest of the way you are in the forest, which on a hot day is nice but also almost completely blocks the view of the water. I ended up riding back via route 28A, which makes for a loop of a little over 30 miles and was not too busy with cars. If you do go this route make sure to take the Ashokan Reservoir Promenade, which parallels route 28A along the shore of the lake for about three miles. The only difficulty is crossing busy route 28 at the end to get back to the parking lot in West Hurley.

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Accordion

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