Pittsfield Inline Skating Trails and Maps

681 Reviews

Looking for the best Inline Skating trails around Pittsfield?

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

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Activities
Length
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18 Results
Activities
Length
Surfaces
Type

Ashuwillticook Rail Trail

11.9 mi
State: MA
Asphalt

Ballston Veterans Bike Path

3.5 mi
State: NY
Asphalt

Black Bridge Trail

2.1 mi
State: NY
Asphalt

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

2.4 mi
State: MA
Asphalt

Connecticut Riverwalk and Bikeway

5.4 mi
State: MA
Asphalt

Erie Canalway Trail

279.5 mi
State: NY
Asphalt, Concrete, Crushed Stone

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

17.3 mi
State: NY
Asphalt, Crushed Stone

Manhan Rail Trail

9.6 mi
State: MA
Asphalt

Mass Central Rail Trail

38 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Sue Grossman Still River Greenway

2.9 mi
State: CT
Asphalt

Uncle Sam Bikeway

3.1 mi
State: NY
Asphalt

Zim Smith Mid-County Trail

9.2 mi
State: NY
Asphalt, Crushed Stone
Trail Image Trail Name States Length Surface Rating
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...
NY 8.4 mi Asphalt
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...
MA 11.9 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
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
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...
MA 3.6 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
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 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
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
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 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...
MA 9.6 mi Asphalt
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...
MA 38 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
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 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
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
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
Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Mid-County Trail, formerly known as the Zim Smith Trail, connects the towns of Halfmoon, Round Lake...
NY 9.2 mi Asphalt, Crushed Stone

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Trails by activity

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...

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...

Mass Central Rail Trail

MA - 38 miles

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...

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

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...

Ashuwillticook Rail Trail

MA - 11.9 miles

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...

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...

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...

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...

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...

Zim Smith Mid-County Trail

NY - 9.2 miles

Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Mid-County Trail, formerly known as the Zim Smith Trail, connects the towns of Halfmoon, Round Lake...

Canalside Rail Trail

MA - 3.6 miles

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...

Manhan Rail Trail

MA - 9.6 miles

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...

Albany County Helderberg-Hudson Rail Trail

NY - 8.4 miles

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...

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...

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...

Columbia Greenway Rail Trail

MA - 2.4 miles

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...

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...

Mass Central Rail Trail

MA - 38 miles

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...

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 - 9.6 miles

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...

Accordion

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...

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...

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...

Canalside Rail Trail

MA - 3.6 miles

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...

Erie Canalway Trail

NY - 279.5 miles

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,...

Zim Smith Mid-County Trail

NY - 9.2 miles

Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Mid-County Trail, formerly known as the Zim Smith Trail, connects the towns of Halfmoon, Round Lake...

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...

Ashuwillticook Rail Trail

MA - 11.9 miles

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...

Albany County Helderberg-Hudson Rail Trail

NY - 8.4 miles

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...

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...

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...

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...

Columbia Greenway Rail Trail

MA - 2.4 miles

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...

Albany County Helderberg-Hudson Rail Trail

NY - 8.4 miles

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...

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...

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...

Accordion

Canalside Rail Trail

MA - 3.6 miles

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...

Erie Canalway Trail

NY - 279.5 miles

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,...

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...

Zim Smith Mid-County Trail

NY - 9.2 miles

Considered "the backbone" of an emerging network of trails in Saratoga County, the Zim Smith Mid-County Trail, formerly known as the Zim Smith Trail, connects the towns of Halfmoon, Round Lake...

Mass Central Rail Trail

MA - 38 miles

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...

Manhan Rail Trail

MA - 9.6 miles

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...

Ashuwillticook Rail Trail

MA - 11.9 miles

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...

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...

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...

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...

Columbia Greenway Rail Trail

MA - 2.4 miles

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...

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...

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...

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...

Recent Trail Reviews

Albany County Helderberg-Hudson Rail Trail

Newly Paved Section

September, 2018 by bhalt299

We had been waiting for the new paved section of trail to open connecting Slingerlands to Voorheesville. It opened and they did a terrific job. There is limited parking at the Port of Albany trailhead but it’s a great ride of about 9.5 miles from there to Voorheesville. At the Voorheesville end the trail ends at a small park that has a new gazebo where an old railway station used to be.

Bog Meadow Brook Nature Trail

Terrible since they've paved

September, 2018 by peggysantiago52

The trail has been ruined since they've paved it. I use to see different kinds of wildlife like, snapping turtles, timber doodle. Now nothing they're all hiding. Totally ruined the nature aspect of the bog.😔 won't go back

Hoosic River Greenway

Hoosick trail

September, 2018 by jerryw22

Nice trail, crusher run, so you have some rough spots. Overall a nice short trail to get your bike out or take a walk. I probably take a fishing pole with me next time on the trail. There are stations to do cardio or other exercises along the trail.

Accordion

Farmington Canal Heritage Trail

Last gap in Cheshire closed

September, 2018 by pausau

Quick update that a stretch of trail less than one mile between Cornwall Av. and West Main St. in Cheshire is now officially opened, avoiding a detour onto Willow St. There is now a continuous, paved, off-road stretch of trail some 25 miles from Temple St. in downtown New Haven to Lazy Lane in Southington.

Farmington Canal Heritage Trail

Love the trails

September, 2018 by jcoombs1230

I am lucky emough to live 1/2 mi from the Farmington Valley Trail and use it quite frequently along with a few of my friends.
I used to ride my horse along this route before it was scheduled for paving for a rail trail. Back then very FEW people used it. Mostly young motorcross kids and horseback riders.
Since it has been paved - horses are now NOT ALLOWED!! (Too bad for us); but as I have moved away from horse riding to personal trail use I am SO HAPPY that I have this wonderful gift in my back yard. There are many many miles and it spans on into southern massachusetts as well.
The trail itself is wonderful; paved, stripe’d and mowed in my area. I have ridden into Mass and south to Simsbury. Before my section was paved I had to load my bike and drive to Simsbury and unload, reload etc. Now, I just hope onto bike (or walk) and go for as long or far as I choose. The scenery is mostly rural, treed and very few homes are seen unless you are crossing streets. I know there are black bears near our home (area) but have not SEEN one ON the trail (daytime use).
It is SUCH a marvelous thing - and I see dozens and dozens of folks biking, walking, & rollerblading. Its a joy to be out in nature!!

Farmington Canal Heritage Trail

Great ride

September, 2018 by olsonz26

Well-maintained, great bike ride. Lots of really cool stops along the way. Beautiful views on the trail north of Hartford.

Hoot, Toot and Whistle Trail

Rock, Root, and Tree

September, 2018 by jennifer81

This trail is not at all as described. It started off on crushed gravel for a few hundred yards. As soon as it entered the woods it became a foot path of a nearly contiguous stretch of single-track biking with (occasionally without) large roots and rocks to navigate. We walked our bikes more than we rode them and went a half mile without getting to the reservoir before finally turning around.

Ashuelot Recreational Rail Trail

Difficult Trail through somewhat scenic country

August, 2018 by natwelch

I started the trail in Hinsdale, and found it reasonably rideable (I use a Specialized hybrid) through Winchester and a few miles beyond. However, the trail started to get rougher including some wet areas. I came to a spot where it followed high tension lines and by the time I got to the monadnock speedway, I was done. I went back to Winchester via Rt 10 and then caught the trail back to my car. Not my favorite trail, but if you have the bike and the inclination, it could be fun for you

Ashuelot Recreational Rail Trail

August 2018

August, 2018 by bdrzyzga

We started the trail in Keene. The first 5 miles were nice, but we had to dodge pretty deep chipmunk holes. The trail is very poorly marked and we missed seeing the Sawyer Crossing Covered bridge which could not be seen by the trail. After 7.5 miles we got turned around by heavy mud, water and a downed tree. I would say this trail might be perfect for equestrians and aggressive mountain bikers.

Fort Hill Recreational Rail Trail

Needs maintenance

August, 2018 by lrhecker47_tl

I tried to access this trail from the northern end which proved impossible. There is no road access until you get to parking areas on either end of the causeway. The trail is not marked with any signage at those places, either, but the track is evident when you cross into the fishing access parking areas off Rt 119. As mentioned, the trail is muddy and filled with puddles during this rainy August, and several trees across the trail. I was not able to reach the northern end because of a very large, multi-branched tree across the trail about a mile south of there. But it was pleasant riding close to the Connecticut River and there were almost no other people on the trail on a weekday.

Valley Trail

Not as advertised

August, 2018 by sarah65

We rode part of this trail while doing some single track riding on the Crosstown trails in West Dover, which connects with this trail. This is not a family friendly paved trail which is the impression I had from the description. I am glad I didn't plan to ride it from Dover to Wilmington with my 9 year old. The part of the trail we saw was single track comparable to a hiking trail. It is not wide, not flat, and not smooth. It is narrow, windy, and filled with rocks and roots. It is not appropriate for little kids or bike trailers.

The Crosstown trails in this area are wide gravel paths. Great for kids who can make it up a decent hill. The single track in the area is nice. It needs some trail maintenance and reroutes along with clearing and trimming. Some areas are nice to ride, others are a mess of roots which are difficult. The trails on the map were very well mapped. It was a nice find on a trip to the area, we will be back!

Valley Trail

NOT ASPHALT!

August, 2018 by mmmzr

NOT ASPHALT! Only one small section (1.5 miles) in Dover is paved... ended up biking Rt100 from Wilmington to Mt. Snow, not much of a shoulder but not much traffic and pretty flat.. nice scenery!

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