Oxford, CT Cross Country Skiing Trails and Maps

1048 Reviews

Looking for the best Cross Country Skiing trails around Oxford?

Find the top rated cross country skiing trails in Oxford, 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
38 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Dirt, Gravel

Billings Trail

3.3 mi
State: CT
Dirt

Briarcliff-Peekskill Trailway

12 mi
State: NY
Asphalt, Dirt, Grass

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Charter Oak Greenway

16.6 mi
State: CT
Asphalt

Columbia Greenway Rail Trail

2.4 mi
State: MA
Asphalt

Derby Greenway

2 mi
State: CT
Asphalt, Dirt

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Crushed Stone

Harlem Valley Rail Trail

17.2 mi
State: NY
Asphalt, Crushed Stone

Hook Mountain/Nyack Beach Bikeway

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

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Jack Harrington White Plains Greenway

1.2 mi
State: NY
Woodchips

Jones Point Path

2 mi
State: NY
Ballast, Dirt

Klara Sauer Trail

1 mi
State: NY
Crushed Stone

Kress Family Trail

3.1 mi
State: CT
Dirt

Larkin State Park Trail

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

Middlebury Greenway

4.5 mi
State: CT
Asphalt

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt
Accordion

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 Mine Railroad Trail

2.2 mi
State: NY
Dirt

Pequonnock River Trail

13.6 mi
State: CT
Asphalt, Crushed Stone

Putnam Trailway

11.9 mi
State: NY
Asphalt

Railroad Ramble

1.7 mi
State: CT
Asphalt, 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

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Sue Grossman Still River Greenway

2.9 mi
State: CT
Asphalt

Tallman Mountain State Park Bike Path

2.1 mi
State: NY
Asphalt, Cinder, Dirt
Trail Image Trail Name States Length Surface Rating
The Air Line State Park Trail winds nearly 55 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...
CT 54.6 mi Ballast, Dirt, Gravel
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
CT 3.3 mi Dirt
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
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
The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
CT 16.6 mi Asphalt
The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
MA 2.4 mi Asphalt
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
A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
CT 16.5 mi Asphalt, Crushed Stone
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
NY 17.2 mi Asphalt, Crushed Stone
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
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail-trail dive through steep rock cuts...
CT 20 mi Crushed Stone
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
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 Ballast, Dirt
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
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
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
The 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 amusement...
CT 4.5 mi Asphalt
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
Accordion
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
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
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 old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
NY 11.9 mi Asphalt
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, 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
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
MA 6.5 mi Asphalt
The Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...
CT 1.2 mi Asphalt, Cinder, Crushed Stone
Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...
CT 2.9 mi Asphalt
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
The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.2 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but you’ll...
CT 4.2 mi Crushed Stone, Dirt
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor Locks. Due...
CT 5.4 mi Asphalt

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Trails by activity

CTfastrak Multi-Use Trail

CT - 4.4 miles

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...

Middlebury Greenway

CT - 4.5 miles

The 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 amusement...

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...

Jones Point Path

NY - 2 miles

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...

Accordion

Klara Sauer Trail

NY - 1 miles

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...

Kress Family Trail

CT - 3.1 miles

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...

Windsor Locks Canal State Park Trail

CT - 5.4 miles

Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor Locks. Due...

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 River Trail

CT - 16.5 miles

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

Southwick Rail Trail

MA - 6.5 miles

The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...

Billings Trail

CT - 3.3 miles

Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...

Stratton Brook State Park Trail

CT - 1.2 miles

The Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...

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...

Harlem Valley Rail Trail

NY - 17.2 miles

Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...

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,...

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...

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...

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...

New Milford River Trail

CT - 5 miles

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....

Sue Grossman Still River Greenway

CT - 2.9 miles

Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...

Railroad Ramble

CT - 1.7 miles

The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...

Farmington River Trail

CT - 16.5 miles

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

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...

Windsor Locks Canal State Park Trail

CT - 5.4 miles

Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor Locks. Due...

Accordion

Billings Trail

CT - 3.3 miles

Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...

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...

Putnam Trailway

NY - 11.9 miles

The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...

Jones Point Path

NY - 2 miles

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...

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...

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...

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...

Middlebury Greenway

CT - 4.5 miles

The 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 amusement...

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...

Charter Oak Greenway

CT - 16.6 miles

The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...

Harlem Valley Rail Trail

NY - 17.2 miles

Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...

Kress Family Trail

CT - 3.1 miles

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...

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...

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,...

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...

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...

Windsor Locks Canal State Park Trail

CT - 5.4 miles

Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor Locks. Due...

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...

Charter Oak Greenway

CT - 16.6 miles

The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...

Middlebury Greenway

CT - 4.5 miles

The 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 amusement...

Accordion

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...

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

CT - 4.2 miles

The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.2 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but you’ll...

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...

Farmington River Trail

CT - 16.5 miles

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

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...

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...

Larkin State Park Trail

CT - 10.8 miles

The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...

Klara Sauer Trail

NY - 1 miles

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...

Putnam Trailway

NY - 11.9 miles

The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...

Harlem Valley Rail Trail

NY - 17.2 miles

Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...

Railroad Ramble

CT - 1.7 miles

The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...

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...

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...

Billings Trail

CT - 3.3 miles

Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...

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...

Kress Family Trail

CT - 3.1 miles

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...

Recent Trail Reviews

Hudson Valley Rail Trail

New Section Great

July, 2019 by wayne7532

Just today rode up to West end of trail. Well maintained. Yes mile markers would be great to have. Crossing main highway was very safe due to walk light set up Thanks for a great safe ride

Niantic Bay Boardwalk

Walks not bikes

July, 2019 by godsmelissa

I give 1 star as a bike trail rating; 4 as a walk. We did this as a walk and that was good. Biking - I would not recommend. Their is sooo much foot traffic a bike Would be a nuisance. On busy days parking can be filled and there is a fee to go to the beach 2018 at least. Walk it the sights are great. We chose to walk back on the side walk adjacent the road so we could see the shops n restaurants

William R. Steinhaus Dutchess Rail Trail

smooth sailing

July, 2019 by pdokuchitz

Heading north from Diddell road is a breeze. Got to the Walkway and were rewarded with a great view and friendly folks! Returning southbound is a little tougher since there is the slight upward grade. Get ice cream or a slice at the frozen caboose!

Accordion

North County Trailway

Scenic but Hilly

July, 2019 by vikkb34

Parked at the trail head in Millwood & rode North. Did total 35 miles. 17 1/2 one way.Rode into the Putnam railway,as they run into each other.The trail is very scenic.You ride pass some towns. But is hilly & can be challenging ..for some..There are sections that are bumpy.. (tree roots) a lot are marked..just have to pay attention..There are some road crossing..all & all we had a good ride..but don't think this trail is for everyone,not just an easy flat trail.. We had lunch at the Tazza cafe on Rt 133,near where we parked,it was great. Toward the healthy side,loved it..

Harlem Valley Rail Trail

A beautiful trail

July, 2019 by john.dischinger

We biked south to north from Wassaic to Millertown(?)....a great way to spend the 4th of July on an absolutely beautiful trail having lunch in the diner then turning around and going back...21 miles felt like 5....

Windsor Locks Canal State Park Trail

very nice 5 mile trail. great for walking. surface is rather bumpy even on my hybrid. can't beat the views. lots of wildlife.

June, 2019 by klinonis

very nice 5 mile trail. great for walking. surface is rather bumpy even on my hybrid. can't beat the views. lots of wildlife.

Farmington Canal Heritage Trail

Trail Status New Haven to Northampton

June, 2019 by petesalomone

Long Wharf to Yale is partially on-road, busy and tricky. Agreements with landowners have been completed and future construction will eliminate some of the on-road. 2018 trail completions in Cheshire and Southington make the trail continuous for 23 miles.
The remaining section in Southington is scheduled for construction in 2020. The Plainville section is currently in design. Construction could start in 2021. It might be phased, so construction might be complete in 2024 or later. When the Southington section is complete it will be relatively safe to ride on-road across Plainville.
From Northwest Dr on the Plainville/Farmington border the trail goes continuously to Main St Westfield about 34 miles. A few railroad bridges in Westfield have to be rebuilt to complete the trail to the Westfield River
North of the Westfield River the railroad is active. The best on-road routes include hilly and traffic. In Southampton the trail will be on the abandoned railroad right of way, but the right of way has not yet been purchased.
Getting to the trail in Easthampton requires about 10 miles of on-road. The last 7 miles of the trail to Northampton are complete

Captain John Bissell Trail

Great hard surface trail, light-traffic roads

June, 2019 by kathleenpwood

We love all of Main St, South Windsor, and it's perfect for a bike ride. I recommend starting at the top of Main St rather than by Chapel Rd as suggested here. It's a sample of old New England with lots of well-maintained vintage homes (including the birthplace of Jonathan Edwards), tobacco barns, fields, & farms. The road itself is a very moderate incline, similar to rails-to-trails. The bike trail alongside I291 is also very easy biking. We only had time to go about halfway on that portion before we needed to head back. An absolutely perfect ride!

Pequonnock River Trail

Nice Ride

June, 2019 by SPanny

We rode this trail on 6/16/19 North from the Tait Road parking lot to its end in Newtown and back, approximately 20 miles total. Almost constantly shaded by trees, very removed from highway traffic, felt like I was in the deep woods at many points. Initial section runs along a ridge and you can look down and see the rivers. Some parts are cinder, some paved, some dirt; there were one or two short sections of gravel; you need a hybrid or a mountain bike (no skinny road bike tires). But overall a very nice ride and worth your time! The section near Tait Road had a number of walkers and families with kids; as we got further north it was much less crowded. As noted, there are several points where you have to cross a road or ride on-road for a short section to get to the next part of the trail, so if you're riding with kids please be aware of this. But we found those sections fairly easy to navigate, even though the signage isn't as good as it could be. There are a few small uphills but they're very short ... just about all flat. Nice to have something like this close to our home in Fairfield County!

Farmington River Trail

Excellent

June, 2019 by yiwang100

This is the 1st trail I rode since started biking 7 years ago. It is still one of my favorites. Close to the north end there is a small town with nice restaurants and a surprisingly good small museum displaying local history. It is well worth a visit.

North County Trailway

Quiet ride so close to NYC

June, 2019 by bkarhoff

My wife and I have been riding the North County Trailway off and on for about 10 years now. Always enjoyable; passes through several small towns but often through unpopulated areas. Trail continues to the south (South County Trailway) and to the north (Putnam County Trailway), so it's possible to start at the NYC border and bike for 40+ miles on well maintained trails.

Farmington Canal Heritage Trail

Very Nicely Paved Trail

May, 2019 by stvatandem

My wife and I rode our tandem from the Brickyard Rd Trailhead northward to the Phelps Rd Trailhead (just short of the MA line). The route is pretty well marked and the pavement is good. Most of the trail/roadway crossings have pedestrian/cyclist buttons to trigger the traffic warning signals and the cars do stop when they see you standing at the crosswalk.
Regarding places to eat: We only saw a sign for one business along the trail. I recommend doing a google search ahead of time to see what's nearby and plan accordingly.

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