Find the top rated cross country skiing trails in New Milford, 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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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...
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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...
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...
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...
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...
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...
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...
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...
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...
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...
The O&W Rail Trail provides a glimpse into the area’s history from the perspectives of both a historical canal and a railroad. The Delaware & Hudson (D&H) Canal carried coal from Honesdale,...
While the Wallkill Valley Railroad no longer carries fruits and vegetables from Ulster County to New York City, trail users can still discover small, family-owned farms and farmers markets serving up...
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...
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...
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...
With vistas of the Catskill Mountains and a vast blue lake, the Ashokan Reservoir Promenade is a stunner. The paved pathway begins in Olivebridge, a hamlet in southeastern New York, and spans just shy...
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...
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...
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,...
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...
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...
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...
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...
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...
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...
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...
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...
While the Wallkill Valley Railroad no longer carries fruits and vegetables from Ulster County to New York City, trail users can still discover small, family-owned farms and farmers markets serving up...
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...
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...
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...
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....
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...
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...
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...
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...
The O&W Rail Trail provides a glimpse into the area’s history from the perspectives of both a historical canal and a railroad. The Delaware & Hudson (D&H) Canal carried coal from Honesdale,...
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...
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,...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
So glad - bit by bit this trail continues to grow.
We lived in Trumbull many years, walked, biked, ran “The Valley” and other sections, including w. Grandkids (now grown - we are GREAT Grandparents now)
So excited, last spring, to finally find safe passage through the Rt 25 interchange area.
Now live in Southside VA
ps. Anyone know about the “cow tunnels” in the Pequonnock Valley, and the tungsten mines??
Thursday, August 15, 2019
Weather upper 80's F, humid. Slightly cloudy.
I drove 2.5 hours last year to arrive here at a trail closed due to insurance problems. Grrrr....
This year it was great. A nice parking lot at either end, the trail between is a nice mix of sun & shade, seclusion and water views. Yes, the asphalt trail can be a bit bumpy, but it is still better than unpaved. I have to admit, the best time to view this trail would be in the autumn when the leaves are at peak color, or after they have fallen for the best views everywhere. But it is worth a visit. You can combine this trail with the Connecticut River Walk in Springfield, MA, which is a bit shorter, but rightr along the river and very nice. It's about a 15-20 minute drive between each trail. I had a wonderful day doing both trails.
Warning: some of the trail photos are not from the Windsor Locks trail that I rode 5 days ago. I do not recognize them.
Warning 2: don't trust the parking lot addresses on Traillink. If you are driving further than half and hour always bring several addresses to try.
This trail is totally inaccessible from the southern trailhead.
My wife and I have been using this trail for years primarily for in-line skating. It is a fantastic trail that is extremely enjoyable each time we are there, however we have noticed over the last few years a real deterioration in the sections in Cheshire and Hamden. The wooden bridges are breaking down that is it dangerous to skate over them, due to the holes that are developing. The inevitable tree roots are getting more and more noticeable and need to be addressed before the ruin the trail any further. The trail needs to be swept and blown regularly, as the stones, gravel and branches all over the trail are noticeable and a hazard to both in-line skaters as well as bikers.
We just rode the Plainville to Simsbury portion of the Farmington Canal Trail and then down the Farmington River Trail. Spectacular. There are a couple of confusing road crossings (1 in Simsbury and another less than clear route just after the bridge in Collinsville). But we loved it. Worth even a long drive. Very shady. Some parts through the woods so not suitable for skinny tire bike.
We rode a total of about 34 miles,17 miles there & back.. We enjoyed this trail,its different then a lot of trails,you are all over the place,riding in residential,the woods,past the Monrovia Nursery,then into the town..but all on paved ground..Good signage.little bumpy in a few spots,but over all pretty good. Mostly flat with a few small climbs.Would like to go back & finish the trail..
Thanks! to the HVRT for resurfacing some of the trail that the tree roots had pushed up pavement. It was nice to be able to ride without having your fillings about ready to come out Thanks HVRT
We stayed at a very nice little inn called Inn at Twaalfskill that has a driveway that connects to the western side of the bridge on the Hudson Valley Trail. The bridge is a little crowded, so you have to take care, but it is worth the spectacular view. The Hudson Valley Trail on the west side and the Dutchess Trail on the east are both well maintained and less crowded than the bridge itself. HIGHLY recommended. The Inn is a great quiet getaway that could not be more convenient for access to the trails.
The trail offers the opportunity to ride in the green and without cars for most stretches, but its views are limited.
The first part through Yonkers is very uninspiring, it looks more like a landfill than a nice trail, so I would definitely skip that part next time. Coming through those Hudson villages is nice, but it also creates the necessity to cross a lot of streets. That wouldn't have been much of a problem if the trail was designed for it, but the way it is now you need to dismount your bike because the curbs are just too high to bike over, so that definitely takes the flow out of the ride.
Signage is poor at some places as well, I would recommend a GPS unit to ride the whole trail. There are also a couple of unbikeably steep sections that also require you to dismount. The final destination, Croton dam, is impressive to see and the highlight of the route.
All in all a very mediocre biking trail, but options are very limited anyway, departing from NYC. I think I won't be riding it again.
I just cycled the new 2.2 mile Heritage Trail extension from Goshen to Hartley Road. It opened July 18 and today (July 29) I did not see a single person on this section going 4.4 miles round trip . Not one. I feel that the county spent a million dollars paving it just for me. I also cycled to other end at Harriman. This is the easiest 30 miles round trip that one can do. Kudos to Orange County for replacing eroded sections with root bumps with smooth new asphalt (lots of the Westchester rail trails sections need this improving). A review below says the trail isn’t 15 each way. It is. The Harriman to Goshen main trail ends at Saint James Place. There are no signs telling you where to pick up this new section. Common sense tells you to follow where the rail line once was. Hint: Railroad Ave. past the old train station. I had to go through an apartment or condominium complex through an open gate and there it is. Beautifully done. This just adds to the greatness that is the Heritage Trail. It is the best within 50 miles of NYC and NNJ. Dutchess Rail Trail to the Walkway Over The Hudson is the best within 100 miles. The Heritage just ends there at Hartley Road. Goshen has lots of place to eat, though, back in the town. Trailside Treats abuts it and is nice (but doesn’t open until noon).
My wife and I rode this train on 7/27/19. We started at the route 2 park and ride, rode south to a point about 2 miles East of East Hampton, then doubled back all the way to the Willimantic Bridge, finally returning to the car. About 30-35 miles total. Very nice trail, well-maintained, tree lined, rural. Few crossroads, cool, not heavily used the day we were there. Please be aware that while there are no big hills, there are a few long steady climbs along the way, especially East of the park-and-ride; think small elevation with a steady,slow climb All told a great trail, would be awesome during Fall color each season. Please also note that you can connect to the Hop River trail just over the Willimantic Bridge.
This lower section of the Air Line is very enjoyable I know the trail goes North through Willimantic, would be curious of people’s impressions of that section.
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