Islip, NY Cross Country Skiing Trails and Maps

867 Reviews

Looking for the best Cross Country Skiing trails around Islip?

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

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Activities
Length
Surfaces
Type
19 Results
Activities
Length
Surfaces
Type

Briarcliff-Peekskill Trailway

12 mi
State: NY
Asphalt, Dirt, Grass

Derby Greenway

2 mi
State: CT
Asphalt, Dirt

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

Hook Mountain/Nyack Beach Bikeway

4.9 mi
State: NY
Asphalt, Ballast, Crushed Stone, Dirt, Gravel

Jack Harrington White Plains Greenway

1.2 mi
State: NY
Woodchips

Joseph B. Clarke Rail Trail

4.1 mi
State: NY
Asphalt

North County Trailway

20.7 mi
State: NY
Asphalt

Norwalk River Valley Trail

5.8 mi
State: CT
Asphalt

Old Croton Aqueduct Trail

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

Old Erie Path

3 mi
State: NY
Dirt, Gravel

Old Putnam Trail

1.25 mi
State: NY
Asphalt

Pequonnock River Trail

13.6 mi
State: CT
Asphalt, Crushed Stone

Quarry Trail

0.1 mi
State: NY
Dirt, Grass

Raymond G. Esposito Memorial Trail

1 mi
State: NY
Crushed Stone

Ridgefield Rail Trail

2.3 mi
State: CT
Gravel

Shoreline Greenway Trail

4.1 mi
State: CT
Crushed Stone, Dirt

South County Trailway

14.4 mi
State: NY
Asphalt, Concrete

Tallman Mountain State Park Bike Path

2.1 mi
State: NY
Asphalt, Cinder, Dirt
Trail Image Trail Name States Length Surface Rating
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
Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...
CT 2 mi Asphalt, Dirt
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
NY 8.5 mi Asphalt
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
CT 48.3 mi Asphalt
While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...
NY 4.9 mi Asphalt, Ballast, Crushed Stone, Dirt, Gravel
The Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...
NY 1.2 mi Woodchips
You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...
NY 4.1 mi Asphalt
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
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
CT 5.8 mi Asphalt
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
The Old Erie Path reveals spectacular views of the Hudson River Valley as the rail-trail rolls along cliffs that border the river’s western shore. Although fairly short, it joins two other...
NY 3 mi Dirt, Gravel
Splayed over 1,146 acres in northwest Bronx, Van Cortlandt Park has a lot going on. The park is New York City's fourth largest and is home to the oldest municipal golf course in America. There are...
NY 1.25 mi Asphalt
The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...
CT 13.6 mi Asphalt, Crushed Stone
The Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...
NY 0.1 mi Dirt, Grass
The Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...
NY 1 mi Crushed Stone
The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...
CT 2.3 mi Gravel
When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
CT 4.1 mi Crushed Stone, Dirt
The South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...
NY 14.4 mi Asphalt, Concrete
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
NY 2.1 mi Asphalt, Cinder, Dirt

Now, More Than Ever, Trails Matter!

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Trails by activity

Hook Mountain/Nyack Beach Bikeway

NY - 4.9 miles

While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...

Norwalk River Valley Trail

CT - 5.8 miles

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...

North County Trailway

NY - 20.7 miles

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...

South County Trailway

NY - 14.4 miles

The South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...

Accordion

Shoreline Greenway Trail

CT - 4.1 miles

When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

Derby Greenway

CT - 2 miles

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...

Farmington Canal Heritage Trail

CT - 48.3 miles

First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...

EPCAL Alternative Transportation Path

NY - 8.5 miles

The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...

Joseph B. Clarke Rail Trail

NY - 4.1 miles

You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...

Pequonnock River Trail

CT - 13.6 miles

The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...

Tallman Mountain State Park Bike Path

NY - 2.1 miles

Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...

Shoreline Greenway Trail

CT - 4.1 miles

When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

Hook Mountain/Nyack Beach Bikeway

NY - 4.9 miles

While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...

South County Trailway

NY - 14.4 miles

The South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...

Old Erie Path

NY - 3 miles

The Old Erie Path reveals spectacular views of the Hudson River Valley as the rail-trail rolls along cliffs that border the river’s western shore. Although fairly short, it joins two other...

Accordion

Farmington Canal Heritage Trail

CT - 48.3 miles

First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...

Tallman Mountain State Park Bike Path

NY - 2.1 miles

Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...

Joseph B. Clarke Rail Trail

NY - 4.1 miles

You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...

Jack Harrington White Plains Greenway

NY - 1.2 miles

The Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...

EPCAL Alternative Transportation Path

NY - 8.5 miles

The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...

North County Trailway

NY - 20.7 miles

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...

Raymond G. Esposito Memorial Trail

NY - 1 miles

The Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...

Pequonnock River Trail

CT - 13.6 miles

The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...

Old Putnam Trail

NY - 1.25 miles

Splayed over 1,146 acres in northwest Bronx, Van Cortlandt Park has a lot going on. The park is New York City's fourth largest and is home to the oldest municipal golf course in America. There are...

Norwalk River Valley Trail

CT - 5.8 miles

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...

Briarcliff-Peekskill Trailway

NY - 12 miles

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...

Ridgefield Rail Trail

CT - 2.3 miles

The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...

Derby Greenway

CT - 2 miles

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...

Old Croton Aqueduct Trail

NY - 26.5 miles

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...

Pequonnock River Trail

CT - 13.6 miles

The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...

Shoreline Greenway Trail

CT - 4.1 miles

When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

Old Putnam Trail

NY - 1.25 miles

Splayed over 1,146 acres in northwest Bronx, Van Cortlandt Park has a lot going on. The park is New York City's fourth largest and is home to the oldest municipal golf course in America. There are...

Derby Greenway

CT - 2 miles

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...

Accordion

Raymond G. Esposito Memorial Trail

NY - 1 miles

The Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...

Joseph B. Clarke Rail Trail

NY - 4.1 miles

You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...

Briarcliff-Peekskill Trailway

NY - 12 miles

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...

EPCAL Alternative Transportation Path

NY - 8.5 miles

The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...

Tallman Mountain State Park Bike Path

NY - 2.1 miles

Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...

Old Croton Aqueduct Trail

NY - 26.5 miles

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...

Norwalk River Valley Trail

CT - 5.8 miles

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...

Old Erie Path

NY - 3 miles

The Old Erie Path reveals spectacular views of the Hudson River Valley as the rail-trail rolls along cliffs that border the river’s western shore. Although fairly short, it joins two other...

North County Trailway

NY - 20.7 miles

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...

South County Trailway

NY - 14.4 miles

The South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...

Farmington Canal Heritage Trail

CT - 48.3 miles

First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...

Ridgefield Rail Trail

CT - 2.3 miles

The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...

Hook Mountain/Nyack Beach Bikeway

NY - 4.9 miles

While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...

Jack Harrington White Plains Greenway

NY - 1.2 miles

The Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...

Quarry Trail

NY - 0.1 miles

The Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...

Recent Trail Reviews

Farmington Canal Heritage Trail

So many great parts. Especially the section that hooks up to Collinsville.Love biking by or over water.

August, 2021 by mvandermeid22

So many great parts. Especially the section that hooks up to Collinsville.Love biking by or over water.

Hudson River Greenway

City Life

July, 2021 by wrogers1

Spectacular views! We road from Dyckman Street Viaduct to The Battery. Hudson River almost always in view. You go right under the George Washington Bridge. Flat, easy ride (note some hills at the north end but you can walk them- they are not long). Along with the sights, always somewhere to stop and get a bite. We generally ride very rural routes so this was a treat for us. Yes, there are a lot of people, motorized scooters, etc. so you have to be alert, but well worth it. We went on a Tuesday, so not too crowded. We parked in a parking garage on Dyckman Street. They were very familiar with cyclists and let you take your time to get your bikes off the rack and get your gear. Bucket list ride for me!

South County Trailway

Poorly renovated

July, 2021 by brandon.field83

Recently repaved in sections, but done sloppily and left bumpy. The northern half of the trail has a lot of sunken and washboard sections that make it unpleasant to ride. From Van Cortlandt Park and about half way up the trail is nice, but from mid-point to where it connects to the north county trail is a mess.

Accordion

Old Croton Aqueduct Trail

Fun Trail

July, 2021 by sarah65

As described, this trail varies from a wide gravel path to a single track dirt track with grass. We started in Tarrytown and went south. This is not a trail for a road bike but you are ok on a gravel bike as long as you are comfortable with rough spots and roots. The trail has lots of road crossings and they vary from neighborhoods where the cars have stop signs to steep hills where no one stops. Almost all have large granite curbs that you have to dismount to lift your bike over. As long as you are cautious you are ok. We made it to Yonkers when we turned around due to a raccoon which was blocking the trail and threatening to attack. Others on the trail kept going and one group was going all the way to NYC. We rode a bit of the River Walk as well which looks like it connects the southern part of this trail with the northern.

There is a bathroom at the Keepers House along with a museum and lovely docents who had lots of fascinating information about the aqueduct.

This was a fun outing to try something new but will likely not be on our list of gravel trails we love to ride and go to frequently.

Hook Mountain/Nyack Beach Bikeway

Nice Sunday Ride Along Hudson

July, 2021 by c.landara2

5 miles of hilly terrain along the river from Nyack to Haverstraw that consists of mostly stone dust with some asphalt. A couple climbs and descents are steep but not a problem for more experienced riders. If you are going to attempt with a road bike go with a bigger tire. The 28mm Armadillos worked well for me. Watch out for pedestrians, especially on the downhill sections.

Setauket-Port Jefferson Station Greenway Trail

Great trail for staying out of traffic.

July, 2021 by tlarsenette

This is a great trail for biking. Lots of hills so bring your ‘A’ game. You can also rent a bike from Pedego a tenth of mile away from the trailhead. The evoked will get you Thru the hills no problem. Pedego Stony Brook in East Setauket 690 NY 25A.

Hudson River Greenway

Easy access from CT

July, 2021 by smpfoley

I drove to Inwood from New Haven - easy access to parking garages off Dyckman St (Henry Hudson Parkway). The path is marked 'Empire State Greenway' not the Hudson River Greenway, just follow the signs as there are two bike paths under the Parkway - don't follow the one closest to the river, that's a short path that dead ends.

For the beginner, if you have the mojo and are motivated, you can make it to Battery Park and back to Inwood with plenty of nourishment and breaks. Speaking from experience. I would bring something to lay on as there are plentiful grassy areas to lay a blanket to take a break.

South County Trailway

too bumpy

June, 2021 by cesnea

most of the trail is located right along the highway so it’s kind of loud. At least 30% of the trail badly needs maintenance lots of bumps sink holes and cracks. Three stars is all this trail deserves.

North County Trailway

A very well maintained trail with okay views

June, 2021 by robert.richter89

I recently rode the entirety of the North County Trailway starting in Elmsford and ending at Somers. The entire trail is paved and in perfect condition, no cracks, bumps or tree roots in sight. Starting in Elmsford makes the return trip significantly easier. Given the completion of the Empire State Trail new signage and mile markers have been installed. There are a few towns along the way for food and there were two major trailheads with bike repair stations but no public water or bathrooms that I could see.

I rode on a very hot day but most of the trail is shaded which provided great relief. The on-road sections mentioned in the description have been separated with a guard rail so no riding with traffic. There are a handful of road crossings, some busy, but I found drivers to be very polite. My only criticism is that the scenery is typical rail trail; forests, streams, some farmland and residential areas. All very nice to look at but nothing breathtaking.

Vanderbilt Motor Parkway

closed till Fall 2021

June, 2021 by lynbrook_greg

They are in the process of re surfacing the trail and the sign says completion Fall 2021.

Setauket-Port Jefferson Station Greenway Trail

review

May, 2021 by jg5z3gd3ed

Nice and smooth paved path. Is hilly at certain points. Crosswalks are safe, with pedestrian flashing lights that are supposed to auto activate. 2 or 3 not working properly, 1 or 2 were.

Saddle River County Park Bike Path

Nice trail but…

May, 2021 by fjd8njjfp4

A LOT of walkers and joggers on the weekend. Trail is paved with a few options for different routes. Mostly very level.

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