Shirley, NY Cross Country Skiing Trails and Maps

525 Reviews

Looking for the best Cross Country Skiing trails around Shirley?

Find the top rated cross country skiing trails in Shirley, 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
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10 Results
Activities
Length
Surfaces
Type

Farmington Canal Heritage Trail

49.1 mi
State: CT
Asphalt

Pequonnock River Trail

14.5 mi
State: CT
Asphalt, Crushed Stone

EPCAL Alternative Transportation Path

9.28 mi
State: NY
Asphalt

Larkin State Park Trail

10.8 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

Shoreline Greenway Trail

4.6 mi
State: CT
Crushed Stone, Dirt

Derby Greenway

1.97 mi
State: CT
Asphalt, Dirt

Jack Harrington White Plains Greenway

1.2 mi
State: NY
Woodchips

Norwalk River Valley Trail

12.2 mi
State: CT
Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel

Ridgefield Rail Trail

2.3 mi
State: CT
Gravel

Northport Rail Trail

0.75 mi
State: NY
Asphalt, Crushed Stone, Dirt
Trail Image Trail Name States Length Surface Rating
Closure notice: During the week of July 7th, the FCHT will be closed due to repaving from Copperhill Road to the Suffield line and then from RT. 189 to Floydville Rd. First a canal, then a...
CT 49.1 mi Asphalt
Note: ALL Trumbull town parks require permit parking stickers year-round (also noted on the signboards at each park entrance).  The Pequonnock River Trail is the formal name for this developing...
CT 14.5 mi Asphalt, Crushed Stone
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 9.28 mi Asphalt
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. About the Route Horseback riders use this trail frequently and...
CT 10.8 mi Cinder, Crushed Stone, Dirt, 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 4.6 mi Crushed Stone, Dirt
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 1.97 mi Asphalt, Dirt
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
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 12.2 mi Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel
The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. About the Route The trail passes among suburban acreages, along a creek at one...
CT 2.3 mi Gravel
The Northport Rail Trail runs for 0.75 miles in the suburbs of Northport on Long Island, NY. About the Route The northern end of the Northport Rail Trail is located along Elwood Rd. where a...
NY 0.75 mi Asphalt, Crushed Stone, Dirt

Recent Trail Reviews

North Shore Rail Trail

Love the trail, but.............

August, 2025 by pawerfel

Great trail, ride it frequently with my wife. Good workout for 22 miles. Main issue is not the road crossings; we ride many trails with more crossings than this, but on those, the towns take down the brush and you can see cars approaching the intersections. On this trail, you pretty much have to stop and inch out into the road to see these cars, many of whom are not "impressed" by the flashing yellow lights that you need to push a button for. Many drivers are looking at their phones rather than the road these days. You must appraoach these intersections as if you are invisible. Be safe

Farmington Canal Heritage Trail

Needs Repaving

July, 2025 by dave36

Haven't ridden the trail since 2023. Rode from Cheshire down to New Haven, Saturday July 19th. Absolutely awful; entire section needs repaving and upkeep. Constant cracks in pavement and much debris on surface; plus glass and homeless down by the Wharf. Connecticut should take notice from Mass and NY on trail up keep. Both states's trail are far superior to CT. Also, difficult to navigate at trail end in New Haven if you don't know the city; poor signage.

Setauket-Port Jefferson Station Greenway Trail

Short Ride But Hilly

July, 2025 by z4g9gshqpr

Only about 7 miles round trip but a lot of gear changing and climbing! Great workout.

Accordion

Pequonnock River Trail

great trail with a mix of everything

July, 2025 by riverahorsemanship

Use gps route its not well marked like others have said but part of the fun was planning the route and then finding your way as you go.

Setauket-Port Jefferson Station Greenway Trail

Nice Path with Some Hills

July, 2025 by bob.dellago

The path is nicely paved and a lot of it goes thru wooded areas. There are a few hills that can challenge the casual rider.

EPCAL Alternative Transportation Path

great trail

July, 2025 by peter330

Great trail for riding. No MVs.

Farmington Canal Heritage Trail

Quick notice: July 7 - 13: Section will be closed

July, 2025 by andrix

Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.

Farmington Canal Heritage Trail

Completed through New Haven

June, 2025 by tswetts

I just rode the trail from Cheshire to New Haven Harbor. It gets confusing because of the lack of signage once you go under the Temple St Garage in New Haven. You get dumped out into a street and don't know where to go. The trail is on the road or sidewalk depending on what you prefer. Take a left onto Grove St. continue to the end and take a right onto Olive ST. Follow Olive St. to the end and pick up the trail again on Water St. Cross Brewery ST and take a right to continue on Brewery. Brewery changes to Sargent Drive. Take a left to go under I95 and the water will be in front of you. If you take a right and continue down for a little, along the water's edge, you will find dozens of food trucks to buy lunch before a return trip. It was well worth the trip.

Setauket-Port Jefferson Station Greenway Trail

Saw 2 Deer on Trail!

May, 2025 by mx546x87dm

This morning May 25, 25 we saw a doe and larger buck between east of Old Town Road.

Ellen Farrant Memorial Bikeway

Taking credit after all these years

May, 2025 by maryjofrohlich

Artie Pescov and I were the initiators of this bike path when I was 17 years old ( I am 70 yo now) and he was 16 yo. I lived on Pine street backing Cedar Creek Park ( old timers would know our property because we had a chicken farm and the hens would cross Merrick Rd. The diner is now there where my grandparents house stood). It was his idea and I had a license. So we travelled around getting signatures to have this bikeway built. We then visited congressman Mr. Murphy ( I think that was his name) of Seaford and he loved the idea. Well, it went through and Artie and I never heard another word about it. Other people (adults not teens like us) took credit for it. However, I am glad that this bikeway still exists! I have long left Long Island but still good memories.
Mary Jo (Masone) Frohlich

Farmington Canal Heritage Trail

A few signs hold it back from five stars

April, 2025 by robert.richter89

I rode the entire northern section of the Farmington Canal Trail from Plainville into MA on a windy Easter Sunday. The trail itself is fully paved, in very good overall condition (there are a few bumps and cracks but nothing major). Simsbury offers a great stopping off point to get refreshments just a quick turn off from the trail. The scenery changes from light industrial parks, residential, marshes, a little farmland and some nice wooded areas.

I have one complaint that prevents this from being a five star trail. The signage could be better. There are times in the more urban areas that I lost the trail, a quick look at Google Maps got me back on and I never was too lost. There are a few signs that were helpful so just a few more would make this a five star trail.

Mosholu-Pelham Greenway

long but decrepit

April, 2025 by vbergerg_tl

Hadn’t ridden in at least 10 years; took it out from Van Cortlandt Park to Orchard Beach, City Island and the Country Club/Pell mansion areas . It is now in horrid shape. Patches bumps ruts. And more hills than I remembered LOL but that’s on me. But the bumps and holes do make hills harder. And also road crossings. No more FOMO

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Accordion

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