Pittsfield, MA Dog Walking Trails and Maps

791 Reviews

Looking for the best Dog Walking trails around Pittsfield?

Find the top rated dog walking trails in Pittsfield, whether you're looking for an easy short dog walking trail or a long dog walking trail, you'll find what you're looking for. Click on a dog walking 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

Ashuelot Recreational Rail Trail

21.5 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Ashuwillticook Rail Trail

11.9 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

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Bog Meadow Brook Nature Trail

2 mi
State: NY
Ballast, Dirt

Bridge of Flowers

0.1 mi
State: MA
Concrete

Canalside Rail Trail

3.6 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

Cohoes Heritage Trail

0.6 mi
State: NY
Asphalt

Columbia Greenway Rail Trail

2.4 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)

0.5 mi
State: VT
Gravel

Erie Canalway Trail

291.9 mi
State: NY
Asphalt, Concrete, Crushed Stone

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt
Accordion

Farmington River Trail

16.5 mi
State: CT
Asphalt, Crushed Stone

Fort Hill Recreational Rail Trail

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

Harlem Valley Rail Trail

17.2 mi
State: NY
Asphalt, Crushed Stone

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

9.6 mi
State: MA
Asphalt

Mass Central Rail Trail

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

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

Rocky Hill Trail

0.9 mi
State: MA
Asphalt

Southwick Rail Trail

6.5 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

9.1 mi
State: VT
Asphalt, Dirt, Gravel

West River Trail

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Zim Smith Mid-County Trail

8.9 mi
State: NY
Asphalt, Crushed Stone
Trail Image Trail Name States Length Surface Rating
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...
NY 9 mi Asphalt
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...
NH 21.5 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
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
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
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
CT 1.8 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 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...
MA 0.1 mi Concrete
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 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
The Cohoes Heritage Trail is less than a mile long but serves as a significant local connector: it provides a way for people to travel between the riverfront to the Mohawk Hudson Bikeway. The northern...
NY 0.6 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 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 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...
VT 0.5 mi Gravel
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,...
NY 291.9 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
Accordion
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
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...
NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
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...
NY 17.2 mi Asphalt, Crushed Stone
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, 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 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 Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
MA 0.9 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
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
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
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 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...
VT 9.1 mi Asphalt, Dirt, Gravel
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...
VT 16.1 mi Asphalt, Dirt, Gravel, Sand
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...
CT 5.4 mi Asphalt
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...
NY 8.9 mi Asphalt, Crushed Stone

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

Trails by activity

Recent Trail Reviews

Farmington Canal Heritage Trail

almost 50 miles paves with any scenery is a 5-star trail

September, 2020 by pbundonis

I've logged about 20k miles of road biking across the United States namely in WA, MO, OH, PA, MD and FL, and maybe 10% of that on trails. To get to stay 99% of the time on a car-free trail for almost 50 miles (as a loop) is rare- and to have some scenery- is nearly unheard of. Thrilled to be in CT now and using this as my go-to ride.

Ashuwillticook Rail Trail

Beautiful trail

September, 2020 by nhelmer78_tl

The trail is a must do for all! It is smooth asphalt the whole trail. Virtually flat the whole trail. Lots of beautiful spots for photo opportunities. A great little farm store and deli just seconds off the trail to pick up a fantastic lunch and sweets with picnic tables on the trail just minutes away! This is a must do trail. I can’t wait to go back and ride it again.

Ballston Veterans Bike Path

Does The Trick

September, 2020 by lmerfffud

This is my go to trail. Close to home, well kept, god for biking or walking and have always felt safe on it.

Accordion

Erie Canalway Trail

Amsterdam area

September, 2020 by edpepper99

Trail near Amsterdam is pretty scenic and has potential to be really nice, however, the trail both East and West of Amsterdam was very bumpy in spots with many tree roots pushing thru the old pavement. Some sections need to be repaved.

Southwick Rail Trail

wonderful rail trail

August, 2020 by trainman1957

By far the best bike ride we have ever had on a paved surface!!!

Columbia Greenway Rail Trail

wonderful trail

August, 2020 by trainman1957

This is by far the best rail trail I have ever been on!!!!

Ashuwillticook Rail Trail

Exceptional trail

August, 2020 by earth2wayne

Just go!

Zim Smith Mid-County Trail

A Great Trail

August, 2020 by lughnerson

August 2020
Starting in Round Lake at a wonderful parking lot, I rode and enjoyed the entire trail, which is beautifully asphalt paved. Some nice scenery. Finishing at 5:00 pm the local church was playing more than 5 minutes of various tunes, the longest I have ever hear. Definitely worth a visit.

Champlain Canalway Trail: Schuylerville

Better than the map shows

August, 2020 by lughnerson

August 2020
This short trail surprised me; it is better than you expect. Right along the Hudson River and the lock canal, the scenery is beautiful and the little village is charming. Definitely worth the visit.

Farmington River Trail

I really like this trail, but my only concern is the intersection at RT. 44 and Lawton Road. There's no signs for either the biker or the motorists

August, 2020 by davehmv

I really like this trail, but my only concern is the intersection at RT. 44 and Lawton Road. There's no signs for either the biker or the motorists

Harlem Valley Rail Trail

Great trail

August, 2020 by potterdunn

This was my first time on this trail and it is worth the trip. It is well maintained with a few bumps here and there but nothing to worry about. It is “flat”, but there is an incline to it. The trail from the southern end in Wassaic to Millerton is 11.5 miles and the trail rises 250 feet. So that’s about a .5% incline which is nothing over a short ride but you do feel it a bit over 11 miles. Well, at least my 61 year old legs felt it a bit. Maybe 2/3rds of the trail is under a tree canopy which shades you from the sun on a hot day and provides some blockage on windy days. If I counted correctly, there are 10 road crossings, which works to less than one per mile. And most of the roads are rural roads so you don’t have to stop too frequently. Though the driver of the one car I encountered didn’t even let up in the gas, let only brake or stop. The restrooms in Millerton are closed, I assume due to COVID. There are two porta potties along the trail. One minor negative is there aren’t too many benches along the way if you want to stop, rest, and enjoy the scenery. And the scenery is nice, maybe not the nicest I’ve seen from a trail, but it certainly is a very pleasant ride. For a beautiful 85 degree August Saturday, there weren’t too many people on the trail, though there were other riders. And everyone seemed friendly. I’m not positive if I was suppose to park where I did - dirt parking lot next to the trail in Millerton - but my car was neither towed nor ticketed when I got back so I guess it was okay. There’s parking at the southern end plus a few smaller lots along the way. There are no services along the way but Millerton has restaurants and shops by the trail. And I believe there’s a place to rent bikes as well. They are extending the trail another 8 miles or so north from Millerton with an expected completion date of October, 2020. So once complete, you’ll be able to do a 40 mile round trip.

Ashuwillticook Rail Trail

repacking from adams to Cheshire

August, 2020 by 8br29ttjas

No useful detour. Will be working into fall 2020

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