Find the top rated cross country skiing trails in Pittsfield, 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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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...
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...
Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Trail, sometimes called the Zim Smith Mid-County Trail, connects the towns of Halfmoon, Round Lake Village,...
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...
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
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...
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Stretching east from Northampton, the 10-mile Norwottuck Branch of the Mass Central Rail Trail connects the towns of Northampton, Hadley, and Amherst. Part of the Connecticut River Greenway State...
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
The Schuylerville segment of the 71-mile Champlain Canalway Trail rail runs between Schuyler House, past Lock 5 of the canal and does a loop around the island (Hudson Crossing Park). As of 2011, only...
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...
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along this nearly 12-mile-long paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
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...
More than 8 miles of the planned 9-mile Albany County Rail Trail (also known as the Helderberg-Hudson Rail Trail) is open and paved. Pedestrians and bicyclists may use the trail and, in the winter...
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...
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For family riding and walking, the Tannersville Bike Path offers a 2.7 mile stretch of graded dirt path starting on Clum Hill Road directly across from Cortina Valley. The opposite end is on Bloomer...
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 Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
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...
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along this nearly 12-mile-long paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
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...
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...
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 heavily wooded Lye Brook Falls Trail runs for 2 miles through the Lye Brook Wilderness of the Green Mountain National Forest near Manchester. The blue-blazed hiking trail follows the bed of a...
The Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...
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...
The Saratoga segment of the 71-mile Champlain Canalway Trail includes three disconnected segments near the Hudson River, from Stillwater Township to the town of Saratoga. The longest section is under...
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...
More than 8 miles of the planned 9-mile Albany County Rail Trail (also known as the Helderberg-Hudson Rail Trail) is open and paved. Pedestrians and bicyclists may use the trail and, in the winter...
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...
For family riding and walking, the Tannersville Bike Path offers a 2.7 mile stretch of graded dirt path starting on Clum Hill Road directly across from Cortina Valley. The opposite end is on Bloomer...
The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
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...
This out-and-back rail-trail's beautiful natural setting and informative signage invite visitors to appreciate the importance of wetland habitats. Located just east of downtown Saratoga Springs, the...
Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Trail, sometimes called the Zim Smith Mid-County Trail, connects the towns of Halfmoon, Round Lake Village,...
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The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...
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...
The Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...
A 104-mile rail line was shattered by hurricane in 1938. Today, the corridor is being developed as the Mass Central Rail Trail to be enjoyed by bicyclists, walkers, joggers, and cross-country skiers....
The heavily wooded Lye Brook Falls Trail runs for 2 miles through the Lye Brook Wilderness of the Green Mountain National Forest near Manchester. The blue-blazed hiking trail follows the bed of a...
Inland and east of the Hudson River, the Uncle Sam Bike Trail (also called the Uncle Sam Trail or Uncle Sam Bikeway) largely serves as a trail for residents of Troy. If, however, you are traveling in...
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...
More than 8 miles of the planned 9-mile Albany County Rail Trail (also known as the Helderberg-Hudson Rail Trail) is open and paved. Pedestrians and bicyclists may use the trail and, in the winter...
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...
Ballston Spa's Jim Tedisco Fitness Trail spans 0.5 mile between Front Street and Prospect Street on what was once a railroad bed.
The Erie Canalway Trail will run for 360 miles in upstate New York—from Buffalo in the west to Albany in the east—linking many other communities along the way, including Rochester, Syracuse, Rome,...
This out-and-back rail-trail's beautiful natural setting and informative signage invite visitors to appreciate the importance of wetland habitats. Located just east of downtown Saratoga Springs, the...
The Saratoga segment of the 71-mile Champlain Canalway Trail includes three disconnected segments near the Hudson River, from Stillwater Township to the town of Saratoga. The longest section is under...
The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along this nearly 12-mile-long paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
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...
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...
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...
Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Trail, sometimes called the Zim Smith Mid-County Trail, connects the towns of Halfmoon, Round Lake Village,...
The Schuylerville segment of the 71-mile Champlain Canalway Trail rail runs between Schuyler House, past Lock 5 of the canal and does a loop around the island (Hudson Crossing Park). As of 2011, only...
For family riding and walking, the Tannersville Bike Path offers a 2.7 mile stretch of graded dirt path starting on Clum Hill Road directly across from Cortina Valley. The opposite end is on Bloomer...
This trail seems little-used. Rode a gravel bike starting at the parking lot at the south end. Several trees down in the trail and some puddles and running water (to be fair, it had rained the night before). The trail surface varies and while it’s manageable, this isn’t a trail for someone looking for a leisurely rail trail cruise. Nice views of the Connecticut River.
The entry leads you to believe there is a 9 mile asphalt trail linking two towns in a Vermont valley with just a small gap near the north end. Unfortunately, there is no such thing. The trail is a very confusing series of blue signs which go through the woods on dirt (mud) tracks, over grass lawns with no identifiable trail, and on busy and narrow town roads (the only asphalt on the trail). Talking to locals, we discovered that parts of the trail are used for mountain biking, but that the idea of a continuous trail linking West Dover and Wilmington is a dream that has yet to be realized.
My wife and I rode this trail from one end to the other. The scenery was beautiful, the ride was easy and the people were nice. Lots of lake views. Some hills but not difficult. Parking was a small challenge but not impossible. I would do it again in a minute.
Stayed at the nearby HGI and decided to take the advice of the front desk lobbiest and run the river path. Entered the path by crossing over the ped bridge by the BHF. Soon into the run the path was closed, It looked like the construction was there for some time leaving me to believe the path had been closed for a while. Turned around and went south dodging the overgrowth along the paved path. A few miles lated it terminated. So, u-turned again back to the BHF bridge. Suspect the city has no budget to invest in maintenence. Too bad. Nothing special, but a least I get out there.
From Wassaic to Copake, free parking in Wassaic train lot on weekends. Goes through a few small towns with bike shops including one in Copake. Lots of places to eat in the towns, some country roads tie the rail trails together, a few hills but nothing brutal, beautiful lake, plains, and frams views, and if you don't mind a small hike, check out Bash Bish falls in copake, worth the hike.
November 2017
It was a good trail in the mountains, except for the bumps of leftover railroad ties. One end is a nice train station, the other is North-South Lake Campground, which you can also bike around, but is not a part of this trail. To see the wonderful water fall you have to get off the main trail a very short distance. A nice bridge over a creek too. Yeah, mountain bikes with suspension only.
I rode this last November, during a warm dry Sunday afternoon. It's a fine trail. At one end is a closed ski slope and lodge I think should become a mountain bike downhill business. The other end just seems to ... end on a road. Between is some nice mountain pass, at one point along a creek that wants to eat the trail, so there was a chainlink fence. If you're in the area, go visit this trail and the charming village of Tannersville.
I rode the trail last week starting at the Wassaic Metro-North station (free parking only on weekends and holidays) and ending at Orphan Farm Road. I did continue to Hillsdale but as there was no signage to indicate how to find the newest section from Hillsdale to Black Grocery road, I did it on road.
All-in-all, both of the main completed sections are in very good shape, fine for road bikes. For the on road gap I took Route 22 going north (flatter but fairly busy with high-speed traffic) and the Under Mountain Road- Rudd Pond Road Route (hillier but much less traffic with swimming available at Taconic State Park- Rudd Pond) on my return. The roads were in good shape either way.
Bash Bish Falls State Park off the northern section is well worth the minor detour. Stay on the road to the falls parking lot and in a 1/4 mile (up hill) you're in Massachusetts!
Went to the south access point in Warehouse Point and found no parking lot, no sign, and no trail! Drove through the building construction only to find a fence blocking the trail. So I went to the north end in Enfield and that too was blocked with a locked fence. No sign or other way to know it was closed. Hope someone will keep the status updated in the future!
Although this Bike Path is scenic, it is NOT maintained, it is continues wide cracks in the pavement and huge bumps. I already saw a couple bickers fall because of the neglected pavement. Not only do you risk a fall because of the neglect, you also risk damage to your tires as the bumps & cracks are severe. I have a Road Bike, and changed my tires because of the bumps, also note the bumps also can shift your gears.
Well worth the 1 1/2 hour ride to get to!! We started at the Plainville parking area and decided to take this path to Simsbury and then return the Farmington Canal Path. The River path is beautiful and deserves the 5 stars. It runs along a beautiful river and brought us to the quaint little town of Collinsville. The only issue we had was the path came to an abrupt end at the route 202 & 44 intersection. There were no signs to indicate the street riding. Guessing , we proceeded on the street until we saw the cycling insignia. The only other poor signage is when you come out of the state forest and there is no indication until approx 100 yards that tells you that you're going in the right direction. We were glad we had the Rails to Trails Southern New England Guide Book we could keep referring to!
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