Pittsfield Trails and Maps

Looking for the best trails around Pittsfield?

Find the top rated trails in Pittsfield, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
42 Results
Activities
Length
Surfaces
Type

Albany County Rail Trail

8.4 mi
State: NY
Asphalt, Crushed Stone, Gravel

Ashuelot Rail-Trail

21.2 mi
State: NH
Ballast, Cinder, Crushed Stone, Dirt

Ashuwillticook Rail Trail

11.2 mi
State: MA
Asphalt

Ballston Veterans Bike Path

3.5 mi
State: NY
Asphalt

Billings Trail

3.3 mi
State: CT
Dirt

Black Bridge Trail

2.1 mi
State: NY
Asphalt

Bog Meadow Brook Nature Trail

2 mi
State: NY
Ballast, Dirt

Bridge of Flowers

0.08 mi
State: MA
Gravel

Canalside Trail

3.3 mi
State: MA
Asphalt

Champlain Canalway Trail: Saratoga

1.5 mi
State: NY
Crushed Stone, Dirt

Champlain Canalway Trail: Schuylerville

2 mi
State: NY
Crushed Stone

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

2 mi
State: MA
Asphalt

Connecticut Riverwalk and Bikeway

5.4 mi
State: MA
Asphalt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

East Branch Trail (VT)

5.1 mi
State: VT
Gravel

Erie Canalway Trail

279.5 mi
State: NY
Asphalt, Concrete, Crushed Stone

Farmington Canal Heritage Trail

40 mi
State: CT
Asphalt, Cinder, Crushed Stone, Grass, Gravel

Farmington River Trail

14.9 mi
State: CT
Asphalt, Cinder, Crushed Stone, Dirt

Fort Hill Branch Rail-Trail

7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand
Accordion

Harlem Valley Rail Trail

17.3 mi
State: NY
Asphalt, Crushed Stone

Harrisville Rail Trail

1.6 mi
State: NH
Dirt

Hoosic River Greenway

2.5 mi
State: NY
Gravel

Hoot, Toot and Whistle Trail

0.5 mi
State: VT
Dirt

Jim Tedisco Fitness Trail

0.5 mi
State: NY
Asphalt

Kaaterskill Rail Trail

2 mi
State: NY
Concrete, Dirt, Grass, Gravel

Lye Brook Falls Trail

2.2 mi
State: VT
Gravel

Manhan Rail-Trail

9 mi
State: MA
Asphalt

Mass Central Rail Trail

31.9 mi
State: MA
Crushed Stone, Dirt, Grass

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

Southwick Rail Trail

7.1 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

Uncle Sam Bikeway

3.1 mi
State: NY
Asphalt

Valley Trail

0.8 mi
State: VT
Asphalt

West River Trail

16 mi
State: VT
Gravel, Sand

Zim Smith Trail

7.5 mi
State: NY
Asphalt, Crushed Stone, Dirt
Trail Image Trail Name States Length Surface Rating
About 8 miles of the planned 9-mile Albany County Rail Trail (also known as the Helderberg-Hudson Rail Trail) is now open. Pedestrians and bicyclists may use the trail and, in the winter months, the...
NY 8.4 mi Asphalt, Crushed Stone, Gravel
Given its covered bridges, historical aura and abundant wildlife, the Ashuelot Rail-Trail (a.k.a. Ashuelot River Trail) has plenty to offer. The 21.2-mile route follows the corridor of the Ashuelot...
NH 21.2 mi Ballast, Cinder, Crushed Stone, Dirt
Nestled in the Hoosic River Valley, between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashuwillticook Rail Trail takes its name from a Native American word meaning "the pleasant...
MA 11.2 mi Asphalt
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...
NY 3.5 mi Asphalt
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
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...
NY 2.1 mi Asphalt
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...
NY 2 mi Ballast, Dirt
The Bridge of Flowers is a 400-foot-long former trolley line bridge that has been converted into a garden pathway. Open from April 1 to October 31, the bridge spans the Deerfield River between...
MA 0.08 mi Gravel
Canalside Trail begins at McClelland Farm Road and heads north on the former NYNH&H Railroad, crossing the Connecticut River near its confluence with Deerfield River. Approximately a half mile north...
MA 3.3 mi Asphalt
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...
NY 1.5 mi Crushed Stone, Dirt
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...
NY 2 mi Crushed Stone
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...
MA 0.21 mi Asphalt
Columbia Greenway Rail Trail offers 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts, from Main st, across the Great River Bridge over the Little River to the...
MA 2 mi Asphalt
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...
MA 5.4 mi Asphalt
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...
NY 3.8 mi Dirt
The East Branch Trail is a 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...
VT 5.1 mi Gravel
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,...
NY 279.5 mi Asphalt, Concrete, Crushed Stone
Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...
CT 40 mi Asphalt, Cinder, Crushed Stone, Grass, Gravel
The Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...
CT 14.9 mi Asphalt, Cinder, Crushed Stone, Dirt
At the southern end of the trail a large parking lot at Dole Junction is maintained by the New Hampshire Bureau of Trails. This parking lot also serves as the southern terminus of the Ashuelot Rail...
NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
Accordion
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...
NY 17.3 mi Asphalt, Crushed Stone
The Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...
NH 1.6 mi Dirt
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,...
NY 2.5 mi Gravel
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...
VT 0.5 mi Dirt
Ballston Spa's Jim Tedisco Fitness Trail spans 0.5 mile between Front Street and Prospect Street on what was once a railroad bed.
NY 0.5 mi Asphalt
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,...
NY 2 mi Concrete, Dirt, Grass, Gravel
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...
VT 2.2 mi Gravel
The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...
MA 9 mi Asphalt
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....
MA 31.9 mi Crushed Stone, Dirt, Grass
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...
MA 10 mi Asphalt
In central Massachusetts, the Norwottuck Rail-Trail (formerly the Northampton Bikeway) runs between New South Street in Northampton and the neighborhood north of Look Memorial Park in Florence....
MA 4.9 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 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...
MA 1.4 mi Asphalt
The Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the...
MA 7.1 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
The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New...
CT 2.9 mi Asphalt
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...
NY 2.7 mi Dirt, Gravel
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...
NY 3.1 mi Asphalt
The scenic Valley Trail currently runs nearly a mile through West Dover in southern Vermont on the outskirts of the Green Mountain National Forest. Plans call for continuing the trail further north to...
VT 0.8 mi Asphalt
Following the floodplain of the West River Valley, the 16-mile West River Trail (a.k.a. Railroad Bed Trail) appeals to a wide range of trail users. The rail-trail has a nearly level surface, ideal for...
VT 16 mi Gravel, Sand
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk March 1–November 30."  The 4.5-mile Windsor Locks Canal Trail follows the Connecticut River and the Windsor Locks...
CT 4.5 mi Asphalt
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,...
NY 7.5 mi Asphalt, Crushed Stone, Dirt

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Trails by activity

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 Canal Heritage Trail

CT - 40 miles

Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...

Ballston Veterans Bike Path

NY - 3.5 miles

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...

Harrisville Rail Trail

NH - 1.6 miles

The Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...

Accordion

Redstone Rail Trail

MA - 1.4 miles

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...

Chicopee River Canal Rail Trail

MA - 0.21 miles

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...

Fort Hill Branch Rail-Trail

NH - 7 miles

At the southern end of the trail a large parking lot at Dole Junction is maintained by the New Hampshire Bureau of Trails. This parking lot also serves as the southern terminus of the Ashuelot Rail...

Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

CT - 4.5 miles

Note: Per the State of Connecticut's website, the trail is open from dawn to dusk March 1–November 30."  The 4.5-mile Windsor Locks Canal Trail follows the Connecticut River and the Windsor Locks...

Mass Central Rail Trail (Norwottuck Branch)

MA - 10 miles

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...

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...

Valley Trail

VT - 0.8 miles

The scenic Valley Trail currently runs nearly a mile through West Dover in southern Vermont on the outskirts of the Green Mountain National Forest. Plans call for continuing the trail further north to...

Farmington River Trail

CT - 14.9 miles

The Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...

Albany County Rail Trail

NY - 8.4 miles

About 8 miles of the planned 9-mile Albany County Rail Trail (also known as the Helderberg-Hudson Rail Trail) is now open. Pedestrians and bicyclists may use the trail and, in the winter months, the...

Tannersville Bike Path (Huckleberry Multi-Use Trail)

NY - 2.7 miles

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...

Southwick Rail Trail

MA - 7.1 miles

The Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the...

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...

Champlain Canalway Trail: Saratoga

NY - 1.5 miles

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...

Manhan Rail-Trail

MA - 9 miles

The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...

Ashuwillticook Rail Trail

MA - 11.2 miles

Nestled in the Hoosic River Valley, between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashuwillticook Rail Trail takes its name from a Native American word meaning "the pleasant...

Harlem Valley Rail Trail

NY - 17.3 miles

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...

Canalside Trail

MA - 3.3 miles

Canalside Trail begins at McClelland Farm Road and heads north on the former NYNH&H Railroad, crossing the Connecticut River near its confluence with Deerfield River. Approximately a half mile north...

Mass Central Rail Trail (Norwottuck Branch)

MA - 10 miles

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...

Harlem Valley Rail Trail

NY - 17.3 miles

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...

Black Bridge Trail

NY - 2.1 miles

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...

Accordion

Bog Meadow Brook Nature Trail

NY - 2 miles

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...

Mass Central Rail Trail

MA - 31.9 miles

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....

Farmington Canal Heritage Trail

CT - 40 miles

Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...

Ashuwillticook Rail Trail

MA - 11.2 miles

Nestled in the Hoosic River Valley, between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashuwillticook Rail Trail takes its name from a Native American word meaning "the pleasant...

Hoosic River Greenway

NY - 2.5 miles

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,...

Fort Hill Branch Rail-Trail

NH - 7 miles

At the southern end of the trail a large parking lot at Dole Junction is maintained by the New Hampshire Bureau of Trails. This parking lot also serves as the southern terminus of the Ashuelot Rail...

Lye Brook Falls Trail

VT - 2.2 miles

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...

Hoot, Toot and Whistle Trail

VT - 0.5 miles

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...

Uncle Sam Bikeway

NY - 3.1 miles

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...

Manhan Rail-Trail

MA - 9 miles

The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...

Bridge of Flowers

MA - 0.08 miles

The Bridge of Flowers is a 400-foot-long former trolley line bridge that has been converted into a garden pathway. Open from April 1 to October 31, the bridge spans the Deerfield River between...

Redstone Rail Trail

MA - 1.4 miles

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...

Ballston Veterans Bike Path

NY - 3.5 miles

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...

Norwottuck Rail-Trail (Francis P. Ryan Section)

MA - 4.9 miles

In central Massachusetts, the Norwottuck Rail-Trail (formerly the Northampton Bikeway) runs between New South Street in Northampton and the neighborhood north of Look Memorial Park in Florence....

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...

West River Trail

VT - 16 miles

Following the floodplain of the West River Valley, the 16-mile West River Trail (a.k.a. Railroad Bed Trail) appeals to a wide range of trail users. The rail-trail has a nearly level surface, ideal for...

Lye Brook Falls Trail

VT - 2.2 miles

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...

Connecticut Riverwalk and Bikeway

MA - 5.4 miles

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...

Mass Central Rail Trail

MA - 31.9 miles

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....

Kaaterskill Rail Trail

NY - 2 miles

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,...

Accordion

Champlain Canalway Trail: Schuylerville

NY - 2 miles

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...

Farmington River Trail

CT - 14.9 miles

The Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...

Manhan Rail-Trail

MA - 9 miles

The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...

Sue Grossman Still River Greenway

CT - 2.9 miles

The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New...

Columbia Greenway Rail Trail

MA - 2 miles

Columbia Greenway Rail Trail offers 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts, from Main st, across the Great River Bridge over the Little River to the...

Southwick Rail Trail

MA - 7.1 miles

The Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the...

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...

Mass Central Rail Trail (Norwottuck Branch)

MA - 10 miles

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...

Harlem Valley Rail Trail

NY - 17.3 miles

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...

Ashuelot Rail-Trail

NH - 21.2 miles

Given its covered bridges, historical aura and abundant wildlife, the Ashuelot Rail-Trail (a.k.a. Ashuelot River Trail) has plenty to offer. The 21.2-mile route follows the corridor of the Ashuelot...

Harrisville Rail Trail

NH - 1.6 miles

The Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...

Champlain Canalway Trail: Saratoga

NY - 1.5 miles

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...

Chicopee River Canal Rail Trail

MA - 0.21 miles

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...

Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

CT - 4.5 miles

Note: Per the State of Connecticut's website, the trail is open from dawn to dusk March 1–November 30."  The 4.5-mile Windsor Locks Canal Trail follows the Connecticut River and the Windsor Locks...

Hoosic River Greenway

NY - 2.5 miles

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,...

Ashuwillticook Rail Trail

MA - 11.2 miles

Nestled in the Hoosic River Valley, between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashuwillticook Rail Trail takes its name from a Native American word meaning "the pleasant...

Recent Trail Reviews

Ashuelot Rail-Trail

Hybrid compatible; not for a roadbike

August, 2017 by declanmccabe

Hi folks,
I read the reviews and went anyway. Started at the Hinsdale end on Northfield Road and went 10 miles. The trail starts on a private driveway directly across from the gas station. I truly enjoyed my ride. Yes it does have mixed surface conditions; abandoned buildings from some industrial past; and the horse-impacted stretch. But is also boasts spectacular river views, covered bridge worth seeing, and a nice trail bridge to ride over. Best of all, the reviews seem to have kept it quiet and underused.

The worst of it is at about mile 8 where the trail first crosses Old Westport Road and Old Spofford Road. There, the horses have torn up the trail and you go between jarring bumps and deeply worked lose sandy soil that will grab your wheel and bring you to an involuntary stop. These conditions last 1.5 miles or there abouts. I won't ride that stretch again; but such is life with multiuse trails.

After mile 10, I exited the trail on the second crossing of Old Westport Road and used the road to bypass the bike unfriendly portion for my return leg. The road is a pleasant spin through farm country.

Overall I found the trail low gradient, shaded, and with easy road crossings. It's not the place to set the land speed record on your road bike and I would not bring young children. But it is certainly teenager compatible and heck, I had 2 hours to kill near Brattleboro and this was just the ticket.

Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

Bumpy but nice ride by river

August, 2017 by smithsr

As others mentioned a little bumpy from roots. Parking on south end is just beyond an old factory building. Turn down single lane road just before canal. There looks to be a gate across the trail, but there is a bike opening to the right. North end has nicer parking in a small park. Some historical info about canal in park. Trail continues north beyond park. Not sure how far it goes.

Ashuelot Rail-Trail

August 10 2017

August, 2017 by sbabs

Ashuelot river trail north of West St Keene is short but scenic, today we did 15 miles round trip on southern part of Ashuelot river trail south of Keene. The trail is really nice for about 4-5 miles after that you follow the power lines and not the river and the going is not as smooth but OK with hybrid bike. We went as far as Swanzey Lake Rd which you can see from a brown house who's back yard is the trail and that is about 7.5 miles one way and it is mostly flat .

Accordion

Ashuwillticook Rail Trail

Ashuwillticook Trail Serenity

August, 2017 by paisleybird

A well maintained, serene, lakeside, forested and gentle day on asphalt . This scenic ride through small towns was full of reminders of past manufacturing and local efforts to attract more riders of all ages. The Adams town visitor center was brand new.
Lots of benches and fewer picnic tables allowed for stops and lunch breaks.
A polite mix of strolling, riding families, couples, friends and single participants added to a soothing day of healthy exercise!

Farmington Canal Heritage Trail

Farmington Canal Rail Trail (New Section) (NW Dr to Red Oak Hill Rd)

July, 2017 by russccc

Hi All,

They recently put the steel in place for the bridge over CT RT 6 in Farmington for Farmington Canal Rail Trail (FCRT). The section maybe in the maybe done in the fall of 2017? It should be complete rather fast! I scouted it out via car lots of this section done.
Trails, Russ C (tn) "Zenith"

Southwick Rail Trail

Southwick Rail Trail

July, 2017 by russccc

Hi All,
Someone asked where is H2~O??
The WATER FOUNTAIN is just due south of jct Southwick Rail Trail & Sam West Rd. Approximately 5.16 Miles North of the CT/MA Border. The fountain is probably seasonal. Nice Ride From CT Border to Main St Westfield, MA (Shop & Shop) Great Day & Good Time. Execellent Bike Pump & Repair Station at CT Quarry Rd & Phelps Rd Lot. Happy Trails, Russ C (tn) "Zenith"

Lye Brook Falls Trail

Lye Brook Falls Vermont

July, 2017 by rasteidel

Nice 4 plus mile hike for someone 72. Friendly people on the trail and neat falls. Would consider it moderate.

Ashuwillticook Rail Trail

Must Do Ride!!!

July, 2017 by paulsen12

My husband and I did this Trail on July 28th...was beautiful! We did it end to end, started at the Lanesborough parking lot then rode to Adams and back. It was perfect - with a lake to ride by, plenty of pull off benches, pond landscapes. My advice is to start in Adams and ride to/towards Lanesborough, there's a slight incline when you're entering Adams so if you want an easier finish ride towards Lanesborough. Trail is clean & well kept also.

Ashuwillticook Rail Trail

Scenic Easy Ride

July, 2017 by kulickk

Well maintained with beautiful scenery along almost the entire length. Lots of places to sit and rest or view the surroundings. A lot of this trail is dead level so its and easy ride. I parked at one of the two lots at the south end of the trail. Good starting point as there are toilet facilities there.

Farmington Canal Heritage Trail

Best of Connecticut

July, 2017 by nimmorp01

Started in Hamdon and road to Southington. Round trip was 28.04 miles. Rented bicycles from Cheshire bike shop which was all of 50 feet from trail. Trail was nicely paved the entire way except for a very short detour.

Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

Beautiful but rough

July, 2017 by aswinsor

Beautiful ride along the river BUT you better have a very soft seat to absorb the rough surface!!

Harlem Valley Rail Trail

Hillsdale section now paved and open!

June, 2017 by billblum

I rode the newest 1.5 mile section from Anthony Street in Hillsdale to the Black Grocery Road trail head across the town line in Copake. It's a pleasant wooded section and a deer even crossed my path notwithstanding how close the trail runs to a residential section of Hillsdale. I then connected to the Orphan Farms Road to Undermountain Road section via a 3.3 mile detour, mostly on lightly traveled local roads with some gentle hills, to the Orphan Farms trailhead. Apparently this detour will be needed for some time since the plans for crossing both the Roe Jan Creek (near the Black Grocery trailhead) and NY Route 22, on the immediate opposite shore of the creek, have not yet been determined.

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