Callicoon, NY Hike Trails and Maps

664 Reviews

Looking for the best Hike trails around Callicoon?

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

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Activities
Length
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Type
33 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

D & H Canal Towpath

0.4 mi
State: NY
Crushed Stone

Great Valley Trail

4.3 mi
State: NJ
Dirt, Grass

Heritage Trail (NY)

19.4 mi
State: NY
Asphalt, Crushed Stone, Dirt

Parksville Rail Trail

1.3 mi
State: NY
Cinder

Sussex Branch Trail

21.2 mi
State: NJ
Cinder, Dirt, Grass

Timberdoodle Trail

2.3 mi
State: NJ
Crushed Stone, Dirt, Grass, Gravel

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

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

D&H Rail Trail

39 mi
State: PA
Ballast, Cinder, Crushed Stone, Dirt

Iroquois Trail

1.8 mi
State: PA
Crushed Stone

Joseph M. McDade Recreational Trail

31.2 mi
State: PA
Gravel

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
Accordion

Mamakating Rail Trail

3.2 mi
State: NY
Ballast, Cinder, Grass, 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

River-to-Ridge Trail

4.9 mi
State: NY
Gravel

Wood Duck Nature Trail

1.5 mi
State: NJ
Ballast, Crushed Stone, Dirt, Grass

D & H Canal Park

0.6 mi
State: NY
Crushed Stone

Endless Mountains Trail

9.2 mi
State: PA
Ballast, Dirt

Liberty Rail Trail

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

O&W Trail (PA)

32 mi
State: PA
Dirt, Gravel

Port Jervis Branch Trail

1 mi
State: NY
Cinder, Gravel

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel

Liberty Loop Trail

2.5 mi
State: NJ
Crushed Stone, Dirt, Grass, Gravel
Trail Image Trail Name States Length Surface Rating
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
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
The Great Valley Trail, built on the former Lehigh & New England Railroad, offers an unpaved, natural experience through quiet woodlands between the townships of Hampton and Frankford. Although...
NJ 4.3 mi Dirt, Grass
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 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 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 of dirt,...
NJ 21.2 mi Cinder, Dirt, Grass
The Timberdoodle Trail runs along a former railroad corridor through the Wallkill River National Wildlife Refuge for 2.3 miles. It is accessible at its northern end and at a trailhead along the route,...
NJ 2.3 mi Crushed Stone, Dirt, Grass, Gravel
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
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
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 jewel of the...
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
Note: With a surface of large-sized gravel, the trail is not recommended for road bikes or mountain bikes with no suspension.  The Joseph M. McDade Recreational Trail runs nearly the length of the...
PA 31.2 mi Gravel
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
Accordion
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 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 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 channel.”...
NJ 27 mi Ballast, Cinder, Crushed Stone, 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
The Wood Duck Nature Trail, appropriately named for the secretive duck, was made possible through the hard work and dedication of refuge volunteers. This beautiful trail extends about 1.5 miles on a...
NJ 1.5 mi Ballast, 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
The local riding club enjoyed this former rail line, which was purchased in 1944 for a dollar from the Delaware, Lackawanna & Western Railroad, as a bridle trail for many years. It changed management...
PA 9.2 mi Ballast, Dirt
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
The O&W Trail (PA) stretches 32 miles throughout northeastern Pennsylvania. About the Route There are two trails named the O&W: one in New York and this one in Pennsylvania. Although the...
PA 32 mi Dirt, Gravel
The Port Jervis Branch of the D & H Canal & Gravity Railroad Heritage Trail. The City of Port Jervis is one of several communities to rescue a portion of the former D&H Canal. A Aside from the...
NY 1 mi Cinder, Gravel
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
Located in the Wallkill River National Wildlife Refuge, the Liberty Loop Trail is 2.5 miles long with a surface of gravel, grass, dirt, and crushed stone. Some portions may have raised wooden planks...
NJ 2.5 mi Crushed Stone, Dirt, Grass, Gravel

Recent Trail Reviews

Joseph M. McDade Recreational Trail

Addition to very picturesque trail

November, 2025 by kaiser

The trail from Milford start point is on k for a few miles but turns to a rocky narrow trail not suitable for a bike , Start at Conashaugh trail head there is only 1 area where you have to walk down 1 set of stairs and go up another otherwise it get great .I wanted to add although I was able have a good ride on my mountain bike I would not recommend the use of any road bike .

Joseph M. McDade Recreational Trail

Very picturesque good trail .

November, 2025 by kaiser

This is a good trail & I would have enjoyed more if it were warmer and I did not ride in gale force winds. Bikers do yourself a favor from Milford grab a bite or drink as you have no food or drink areas until the end unless you ride when Dingmans campsite is open , you may get something there . Proceed 209 S to Conashaugh trail head unload and go south from there you will have about 18 miles to the end.

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.

Accordion

Sussex Branch Trail

Great For Fall Foliage

October, 2025 by 7zwbq79645

The trail is well maintained. Mostly passable with gravel bike except a small portion around Andover. The section around Andover is also hard to navigate.

D&H Rail Trail

Great trail, with some room for improvement

October, 2025 by ibew241

My wife & I ride from the north end to just south of Steven’s Point. From Steven’s Point south we experienced rough trail conditions including trail-wide mud puddles and ballast stone, nothing like the stone dust conditions to the north. There were still a lot of downed trees along the path from earlier storm damage. Consider becoming a member of the Rail-Trail Council of North East Pennsylvania. They could use your financial help so the trail conditions I mentioned above can be completed. We will definitely be back to rude more of the D&H.

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

Parksville Rail Trail

This trail is lovely there's a little water fall halfway through it we're the railing is and its beautiful

September, 2025 by fay.ridgeway05

This trail is lovely there's a little water fall halfway through it we're the railing is and its beautiful

Sullivan O&W Rail Trail

O&W mountaindale - ferndale

September, 2025 by kaiser

Nice scenic ride . The mountaindale side goes through several abandon like towns nice ride mostly dirt / cinders / crushed stone lots of nice scenery for about 3 miles then you end at the Neversink River where a bridge is out so you have to pedal 7 miles via road to hook up on the Fallsburg side which is paved ,nice trail for 4 miles . Would do again , tables , benches and bike tool areas . No road bike for gravel part

Sussex Branch Trail

diverse & well maintained

August, 2025 by kjfhall61

The trail is ~ 20 miles in each direction. A good mix of paved, gravel, dirt — with minor sections that are “single track”’ish.

Heritage Trail (NY)

Nice trail. Poor signage in Goshen

August, 2025 by ddylla

Overall, a very nice paved trail that’s well maintained but very poor connectivity and signage in Goshen. If not for that poor connection, I would have rated this trail five stars. Well worth checking out and hopefully Goshen will improve that stretch in the future.

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Accordion

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