Find the top rated walking trails in Pittsfield, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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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 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...
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 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...
This asphalt trail is the legacy of an inter-urban trolley system operated by Schenectady Railway Company (SRC) in the early 1900s. To attract visitors on weekends, SRC built an amusement park at...
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
Just north of Albany, the Black Bridge Trail connects the communities of Waterford, Cohoes, and Green Island in eastern New York. As it parallels Delaware Avenue, it is sometimes referred to as the...
Popular with residents of Saratoga County who commute under their own power or love to exercise outdoors, the nearly 9-mile Zim Smith Mid-County Trail is considered the backbone of a growing trail...
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 Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
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...
Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis and community connector for residents living southwest of...
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...
When complete, 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,...
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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...
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...
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 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 Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis and community connector for residents living southwest of...
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
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 scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...
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...
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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...
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 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...
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...
The Kaaterskill Rail Trail offers a beautiful wooded walk through Haines Falls in eastern New York, nestled in the northern Catskills. It begins at the historical Ulster & Delaware Train Station,...
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 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,...
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 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 Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
Just north of Albany, the Black Bridge Trail connects the communities of Waterford, Cohoes, and Green Island in eastern New York. As it parallels Delaware Avenue, it is sometimes referred to as the...
This asphalt trail is the legacy of an inter-urban trolley system operated by Schenectady Railway Company (SRC) in the early 1900s. To attract visitors on weekends, SRC built an amusement park at...
When complete, 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,...
The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...
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...
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...
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 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...
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...
Just north of Albany, the Black Bridge Trail connects the communities of Waterford, Cohoes, and Green Island in eastern New York. As it parallels Delaware Avenue, it is sometimes referred to as the...
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 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...
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 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...
When complete, 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,...
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 Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...
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...
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...
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 well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...
I did the loop today going north on this River Trail then back south on the FCT. The gravel is at mile 12.3 after a little on the road segment but it only lasts about 3/4 mile. I had to go very slowly on the gravel dust because I was on my road bike (22mm) but it was tolerable because it was short (&pretty). At the entrance to the Stratton State Park a sign indicates you can take the road downhill to Simsbury felt safe. froDOWNdown to Simsbury which was much better on thin tires. indicating on esign The on the road section was well marked today - although many of the signs were large temporary ones. I how
Beautiful and no crowded from Amenia to Milerton - 8 plus miles from the parking lot indicated on the map. Trail ends in Millerton - I did not ride along rite 22 to pick up the rail trail again for the final five r so miles, as it is crazy town to ride on Route 22. Overall, a pleasant there and back (I went past the parking lot to make a twenty mile ride). I hope that the trail does get connected and soon.
We are in our 60’s and once or twice a year we like to get away for the weekend and ride a nice rail trail or two. This trail was Perfect. It is excellently maintained, the few roots are so well marked you couldn’t miss them. It’s clean, lots of benches and tables along the way and bathrooms at one end. Plenty of parking at each end and many spots along the way. This is one of the best trails we’ve been on. The best tip I can give is to start in Adams as you’ll appreciate the slight decline of the last two miles coming back. You don’t even notice the slight incline when heading out but tired legs appreciated the break on the way back. 22.8 miles round trip from visitors center in Adams
Enjoyed a ride from Simsbury past the Mass line and back. As always, well maintained, a few frost heaves here and there but nothing major. As we were riding we noticed some trail widening in progress in Simsbury/Granby. The area across the Mass line is very well maintained and passes some fields and a nice golf course. Thoroughly enjoyable!
Instead of the heavily used trails, l looked for one off the beaten path, so to speak. I found this trail searching for NH trails and was somewhat familiar to the area after going to Monadnock Speedway over the years. I didn't realize this trail runs across the entrance to it. After reading a bit, it seems it is partially a paved trail but only near Keene. Figured I would start at the southern end since it's only an hour from where I live. I found the parking area easy enough and figured I'd start the trail from there which is right across the street. I see that the trail goes south a little more but in all honesty, driving on the road getting to the parking area or after leaving, I couldn't see where you actually get to the trail end. Since it's only a quarter mile more, I didn't bother backtracking to figure it out. Trail is unpaved on the southern end and I had read a few people's comments about how they couldn't get past the speedway since the trail isn't maintained all that well in that area. I went up to where it crosses over Rt. 119 (short distance west from the intersection of Rt. 10) then rode back on the highway back to the parking lot. The trail is a mix of grass, gravel, some mud but not much, soft sand and the like. Looks like they just took the tracks out and cleaned it up a bit and said here you go. It wasn't all that difficult to get through the section I did which was about 8 miles, give or take. I used a hybrid bike and had no real issues. I wouldn't recommend a road bike at all. It was a fun ride, saw all the stuff people had mentioned about the old tracks, rail shed and covered bridge. It was a pretty cool ride. I didn't see any other bikers the whole time I rode through the area and only a 2 other people out walking. I did see a couple devices on the side of the trail which had cables running across it. It appeared to be devices to record how much usage, somewhat like you'd see driving a car across a road. Not sure why they are doing this, it's not like I think they're putting too much into this section if this is the state doing this recording. I wonder if by chance it was paved that it would bring more people in. However, I don't see where those using it would help economically since it's not going into any business areas. Some trails have businesses near it like ice cream stands or convenience stores but this section is not designed for that. Time will tell I guess. Maybe I'll go back next year to see if I can get past the race track area. A good Sunday ride through the woods.
Rode one way approx 7 miles starting in Amsterdam. While pedaling under the thruway overpass, it smelled like feces/urine. This area has an abandoned building and an adjacent overgrown wareyard with debris piles, junk and very weedy. Approx 1/3 mile past the overpass we stopped to look at map and weather app (the clouds were looking ominous) and I see a large man riding toward us (up until that point we saw no-one else on the trail). As he passed us grunting and snarling at us, I noticed he was filthy with dirty hair and face. He rode past us and less than 30 seconds later when I looked down the trail, he had disappeared into the brush (this is a straightaway section - you can see a long way). We turned around and within 10 minutes the downpour was upon us. We were soaked when we arrived back in am-dam.
My advice: do not pedal this section by the overpass alone. This man had no good reason to pursue us, then growl/grunt when passing us and then disappear back into the brush. If I had been solo riding, I can only speculate on a different outcome. He is living under/by the overpass. We apparently pedaled thru his "area".
First what this isn't...an "off road" trail. No dirt or gravel.
However if you want a beautifully maintained paved bike path, then you found it.
Extremely flat with a variety of scenery from forest to wetlands to lakes to old industrial.
A lovely ride
This entire trail has been paved for years.
I'm a local who lives just down the mountain and I often frequent the trail. I love the tracks that remain from the some of the first times our area was booming. Tourists seem to hate them, which is ironic because that's how they were able to get to the area back in the day.
September 5 2019. Best Rail to trail we have ridden on. We started at the parking area in Hamden and went north 12 miles. Most of the trail was smooth as fresh tar. We almost did not do this trail because of the reviews but they were wrong. If you like smooth riding and well marked, this is the trail for you
This is the first of a multi-part review, since the trail is so long. It takes me and hour and a half to drive from New Paltz, NY to one of the parking areas.
Last year I rode the section from the Corning Center in Albany along the Hudson River to end at a parking lot in Watervaliet. Right next to the the river, there is a lot to see and hear on this paved trail, as the highway is sometimes very close. There are plenty of areas to stop and touch the water while on a break. Just do it sometime anytime. I would like to revisit this section after the leaves have fallen, just before winter.
Last month I rode from the through the Albany suburbs of Watervaliet, Green Island, and Cahoes. Though it is fairly flat and well paved, it is totally on-street section of the trail. One nice side trip is north up to Waterford, which goes over several bridges to Van Schaich Island and Peebles Island. When you cross the steel bridge you can see the beginning of the actual canal and its first lock near the Waterford Harbor Visitor Center. Just go down Cannon Street.
Last week, Tuesday August 20, 2019 I went to the section that includes the towns of Latham and Colonie, turning around at Lock 7 on the Mohawk River. This is a very nice section of the trail, good pavement, mostly shady and offers a few nice views of the Mohawk River. There is a short on-road section in Dunsbach Ferry where you ride underneath Route 87. Then a significant hill back to the trail. Headed west, from the Lions Park in Niskayuna ( a good parking area) there is one very straight and flat section of about a mile or so for time-keepers and racers. Lock #7 is a pleasant park to stop for a break and watch the boats navigate the rise or fall of the lock, next to a waterfall.
It may take several years for me to complete the entire Erie Canal trail, but it is a fun goal.
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