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Westport, CT Cross Country Skiing Trails and Maps

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Looking for the best Cross Country Skiing trails around Westport?

Find the top rated cross country skiing trails in Westport, 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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Name
Length
Most Popular

Air Line State Park Trail

60.3 mi

State: CT

Ballast, Crushed Stone, Dirt, Gravel

Farmington Canal Heritage Trail

49.1 mi

State: CT

Asphalt

Harlem Valley Rail Trail

26.4 mi

State: NY

Asphalt

Heritage Trail (NY)

19.4 mi

State: NY

Asphalt, Crushed Stone, Dirt

Hook Mountain/Nyack Beach Bikeway

4.9 mi

State: NY

Asphalt, Ballast, Crushed Stone, Dirt, Gravel

Joseph B. Clarke Rail Trail

4 mi

State: NY

Asphalt

Kress Family Trail

3.1 mi

State: CT

Dirt

Litchfield Community Greenway

2.5 mi

State: CT

Boardwalk, Crushed Stone, Dirt

Maybrook Trailway

28.6 mi

State: NY

Asphalt

North County Trailway

20.7 mi

State: NY

Asphalt

Old Erie Path

3 mi

State: NY

Dirt, Gravel

Pequonnock River Trail

14.5 mi

State: CT

Asphalt, Crushed Stone

Putnam Trailway

11.8 mi

State: NY

Asphalt

Raymond G. Esposito Memorial Trail

1 mi

State: NY

Crushed Stone

South County Trailway

14.4 mi

State: NY

Asphalt, Concrete

Tallman Mountain State Park Bike Path

2.1 mi

State: NY

Asphalt, Cinder, Dirt

West Essex Trail

3.3 mi

State: NJ

Cinder, Gravel

CTfastrak Multi-Use Trail

4.4 mi

State: CT

Asphalt, Concrete

EPCAL Alternative Transportation Path

9.28 mi

State: NY

Asphalt

Jones Point Path

2 mi

State: NY

Asphalt

Accordion

Larkin State Park Trail

10.8 mi

State: CT

Cinder, Crushed Stone, Dirt, Gravel

Middlebury Greenway

4.5 mi

State: CT

Asphalt

Morris Canal Greenway

4.1 mi

State: NJ

Dirt, Grass

New Milford River Trail

5 mi

State: CT

Asphalt, Crushed Stone, Dirt

Old Croton Aqueduct Trail

26.5 mi

State: NY

Crushed Stone, Dirt, Grass, Gravel

Shoreline Greenway Trail

4.6 mi

State: CT

Crushed Stone, Dirt

Briarcliff-Peekskill Trailway

12 mi

State: NY

Asphalt, Dirt, Grass

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

Ramsey Bike Path

1 mi

State: NJ

Asphalt

Ridgefield Rail Trail

2.3 mi

State: CT

Gravel

Old Mine Railroad Trail

2.2 mi

State: NY

Dirt

Samuel G. Fisher Mount Ivy Environmental Park

2 mi

State: NY

Ballast, Cinder, Dirt, Grass, Woodchips

Klara Sauer Trail

1 mi

State: NY

Crushed Stone

Northport Rail Trail

0.75 mi

State: NY

Asphalt, Crushed Stone, Dirt

Trail Image	Trail Name	States	Length	Surface	Rating
	Air Line State Park Trail The Air Line State Park Trail winds 60.3 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is nearly...	CT	60.3 mi	Ballast, Crushed Stone, Dirt, Gravel	154 reviews
	Farmington Canal Heritage Trail 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	49.1 mi	Asphalt	165 reviews
	Harlem Valley Rail Trail Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful 26.2-mile wooded pathway along the former New York & Harlem Railroad...	NY	26.4 mi	Asphalt	77 reviews
	Heritage Trail (NY) 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	104 reviews
	Hook Mountain/Nyack Beach Bikeway The Hook Mountain/Nyack Beach Bikeway is a scenic trail that runs almost 5 miles along the Hudson River in Rockland County. About the Route The trail runs through Hook Mountain State Park and...	NY	4.9 mi	Asphalt, Ballast, Crushed Stone, Dirt, Gravel	27 reviews
	Joseph B. Clarke Rail Trail The 4-mile rail-trail passes through three downtowns. The quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by woodlands, sanctuaries, and parks. About the...	NY	4 mi	Asphalt	44 reviews
	Kress Family Trail The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...	CT	3.1 mi	Dirt	5 reviews
	Litchfield Community Greenway The Litchfield Community Greenway runs along the former Shepaug Railway railbed in the Town of Litchfield. Operational from 1878 to 1948, the railroad line ran between between Litchfield and...	CT	2.5 mi	Boardwalk, Crushed Stone, Dirt	1 reviews
	Maybrook Trailway The Maybrook Trailway is a paved multi-use trail stretching across Putnam and Dutchess counties in New York state. The trail, which is owned and was built by Metro North Rail, occupies the former...	NY	28.6 mi	Asphalt	46 reviews
	North County Trailway At just over 20 miles, the North County Trailway is the longest of four rail trails created from the former New York Central Railroad’s Putnam Division line. The trail travels through communities in...	NY	20.7 mi	Asphalt	69 reviews
	Old Erie Path 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	10 reviews
	Pequonnock River Trail 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	63 reviews
	Putnam Trailway The old New York Central rail line that ran from the Bronx to communities north of the city in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends, tourists...	NY	11.8 mi	Asphalt	55 reviews
	Raymond G. Esposito Memorial Trail 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	6 reviews
	South County Trailway The South County Trailway rolls 14.4 miles through one of the most dense parts of greater New York City, though its backcountry route through pocket woodlots, parks, and golf courses and along...	NY	14.4 mi	Asphalt, Concrete	55 reviews
	Tallman Mountain State Park Bike Path 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	2 reviews
	West Essex Trail The West Essex Trail runs for 3.3 miles through Cedar Grove, New Jersey along the former rail bed of the Caldwell Branch on the old Erie-Lackawanna Railroad. About the Route The trail's northern...	NJ	3.3 mi	Cinder, Gravel	23 reviews
	CTfastrak Multi-Use Trail A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...	CT	4.4 mi	Asphalt, Concrete	9 reviews
	EPCAL Alternative Transportation Path 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	11 reviews
	Jones Point Path The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...	NY	2 mi	Asphalt	23 reviews

Accordion

Larkin State Park Trail 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	37 reviews
Middlebury Greenway The 4.5-mile Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an...	CT	4.5 mi	Asphalt	18 reviews
Morris Canal Greenway In the early 1830s the Morris Canal opened across northern New Jersey, from Phillipsburg on the Delaware River to Newark, and later to Jersey City on the Hudson River. It provided a thoroughfare for...	NJ	4.1 mi	Dirt, Grass	3 reviews
New Milford River Trail 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	7 reviews
Old Croton Aqueduct Trail 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	18 reviews
Shoreline Greenway Trail 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	3 reviews
Briarcliff-Peekskill Trailway 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. About the Route The trailway...	NY	12 mi	Asphalt, Dirt, Grass	5 reviews
Derby Greenway 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	13 reviews
Jack Harrington White Plains Greenway The Jack Harrington White Plains Greenway's name reflects the honorfic for 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	6 reviews
Norwalk River Valley Trail 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	7 reviews
Ramsey Bike Path The Ramsey Bike Path is a recreational path built on the former Paterson to Suffern trolley line right-of-way. The path extends along a north-south route from one end of Ramsey to the...	NJ	1 mi	Asphalt	4 reviews
Ridgefield Rail Trail 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	14 reviews
Old Mine Railroad Trail Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...	NY	2.2 mi	Dirt	3 reviews
Samuel G. Fisher Mount Ivy Environmental Park The Samuel G. Fisher Mount Ivy Environmental Park offers a hiking trail along a former right-of-way of the NY & NJ Railroad. The trail is entirely wooded and offers views of nearby wildlife and...	NY	2 mi	Ballast, Cinder, Dirt, Grass, Woodchips	4 reviews
Klara Sauer Trail The Klara Sauer Trail (formerly known as the Beacon Riverside Trail) runs for 1 mile along the Hudson River on the west side of New York's village of Beacon. The trail occupies the same corridor as...	NY	1 mi	Crushed Stone	5 reviews
Northport Rail Trail 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	0 reviews

Recent Trail Reviews

Maybrook Trailway

Great Trail

October, 2026 by roboconnor

Rode October 2026, easy access off 84, beautiful Fall day, scenery is varied, paved surface was flawless.

William R. Steinhaus Dutchess Rail Trail

Easy access, clean blacktop and nearly unlimited distance in either direction! Outside of the Morgan Park entrance this is the best bet!

October, 2026 by jhesse.m.lamb

Easy access, clean blacktop and nearly unlimited distance in either direction! Outside of the Morgan Park entrance this is the best bet!

Air Line State Park Trail

Beware

October, 2026 by 8jp5rr55yf

So I started this trail in Portland, Connecticut, and about 3 to 4 miles into it. It stops at a marsh river area. There is no sign to tell you that it does or what detour to take. You would have to get on the main road to avoid this section. And the way people drive on that road I wouldn’t trust it. From what I heard, they were supposed to build a bridge over this section but said they were waiting for EPA to be involved which was years ago so I would highly recommend that you start in East Hampton for continued access.

Accordion

Naugatuck River Greenway

Nice area of Waterbury

October, 2026 by santos92476

Decent walk and view. As of October 2026 bathrooms are not open ever.

Pompton Valley Rail Trail

scooters

September, 2026 by mythreesonsccb

Rode an electric scooter, granddaughters had their scooters. Excellent surface! So easy to park by the old train station- 10 feet to the trail. Beautiful afternoon! ¿

Maybrook Trailway

Great ride!

September, 2026 by joglazewski

Rode Pawley Trailhead to Hopewell Junction and back. Perfect, smooth, clear, pavement. No downed trees . Few easy road crossings, shady throughout. Nice lunch at Daddy Os in Hopewell Junction.

Harlem Valley Rail Trail

A beautiful trail, but not quite complete

September, 2026 by basil1986

We did this trail in two days. We learned that it is not quite complete from Hillsdale to Wassaic. Trail is closed from Black Grocery Road to Orphan Farm Road about 1.5 miles. So be warned that as of Sept 15 you can’t quite go completely through YET. Above Millerton and below are almost two completely different trails so we were happy to be able to stop and explore at our leisure. Above is really farm and marsh lands while below has more towns and historical things to see and do. Millerton, has many places to eat and a great mid stop. The leaves are not turning yet but will be beautiful in the colorful fall. I heartily recommend the ride.

Saddle River County Park Bike Path

great park but…

August, 2026 by lombardi3716

I’ve gone a few times to ride my bike however I’ve almost got taken out by people on racing bikes and think they are in a triathlon..not cool

Air Line State Park Trail

geminird review misleading

August, 2026 by atclaw

This rider was going Northeast from Willimantic towards Hampton NOT Southwest from Willimantic to East Hampton. Having ridden both stretches I can say his description is completely wrong about the gorgeous and open riding Southeastern route and not completely wrong but somewhat overly harsh about his route which can get iffy for stretches.

Harlem Valley Rail Trail

Beautiful

August, 2026 by trylondm

Rode entire trail roundtrip on a sunny August day. It's a great trail with a great paved surface. Scenic, too. The southern trailhead (Wassaic) has a direct train connection to New York City, so it's just a matter of time before it's discovered by folks from the city for a day's ride.

Town of Millerton in center of trail had the best facilities for a mid-ride break. Copake Iron Works Museum at Taconic State Park and close to the trail also well worth a visit.

North Shore Rail Trail

Crossings

August, 2026 by y4mzd4xprg

Too many roadway crossings for my taste.

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..

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