Pittsfield, MA Dog Walking Trails and Maps

841 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.

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
Type
43 Results
Activities
Length
Surfaces
Type

Albany-Hudson Electric Trail

35 mi
State: NY
Asphalt, Crushed Stone

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
Accordion

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

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

23.2 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

11.5 mi
State: NY
Asphalt
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 Albany-Hudson Electric Trail (AHET) follows a 35-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
NY 35 mi Asphalt, Crushed Stone
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
Accordion
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
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 23.2 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...
CT 5.4 mi Asphalt
Popular with residents of Saratoga County who commute under their own power or love to exercise outdoors, the nearly 12-mile Zim Smith Mid-County Trail is considered the backbone of a growing trail...
NY 11.5 mi Asphalt

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

Albany-Hudson Electric Trail

we’ll maintained

July, 2021 by eckinois

We rode 50 miles on trail and had best rail trail experience ever. Maybe next weeks Rail Trails .org inaugural 5 day ride sponsored to go from NYC to Buffalo NY was reason for pristine surface & great signage but every part of trail was in immaculate condition even after last five days heavy rains.

Manhan Rail Trail

Great! Flat, paved, fairly picturesque

July, 2021 by ajgreenhalgh

I like this trail to walk because it is well paved, flat, no hills, and friendly considerate people especially the bike riders who usually indicate when they are passing me. There is some industrial and kind of dumpy areas that abut the trail unlike where I came from, Woodstock NY, where the paths are pristine and beautiful. However, I like where the trail crosses a bridge across the Mill River just past Veterans Field in Northampton.

Bloomfield Greenway Multi-Use Trail

great ride for beginners

July, 2021 by vegito_ssj22001

This is a great ride for me to test my novice skills. I find myself coming back to here twice a week after work just to get a quick workout in

Accordion

Fort Hill Recreational Rail Trail

Prospect Street to Brattleboro Bridge

July, 2021 by aldcon_tl

Started at Prospect Street boat launch and road north. First mile or two of trail is wide and gravel with potholes. Nice scenery next to river. I'd score this part of the trail a 3. From mile 2 to 3 the trail is still wide but mostly grass with two dirt tracks (a car width apart). Grass is about 8 to 12" tall. Hard to see some bumps and defects. I'd score this part of the trail a 2. From mile 3.2 to the bridge at mile 4.4 (all distances from Prospect Street) boat launch the trail is in poor condition and a single track. I'd score this a 1. The bridge is the remnant of an impressive structure. The steel is rusty but in good shape. The timbers are rotting but for those not intimidated they can be walked. It's a shame the bridge isn't being saved for rail trail users. This is a dead end. I wanted to get back on to Route 119. I needed to go back 1.2 miles to find a poor quality side trail that dumped me out behind the Sunoco gas station.
The scenery on the ride was the best for the first 2 miles of the trip. After that, in general, you are inland and not looking to the side. Your focus is on navigating the trail.

Ashuwillticook Rail Trail

Amazing Trail

July, 2021 by cklewis24

We just rode this trail for the first time and we will certainly be back. Amazing views, paved surface, and plenty of opportunities to stop and sit. The only improvement I would suggest would be to add mile markers.

Ballston Veterans Bike Path

quick stop for a ride

July, 2021 by lindarkv

Easy parking. Short, flat straight ride along the water. Very exposed, not great for a hot day.

Albany-Hudson Electric Trail

Parking for trail heading southeast

June, 2021 by ellavigna

Per the advice of the other reviewers, we started from Schodack. We parked at the SEFCU right off the I90 exit for Schodack (if heading from west take right off exit). There is gas station/Dunkin’ Donuts right next to the exit and the SEFCU is right next to that. This way we avoided on road sections in East Greenbush. There are some hills between Schodack and Nassau but they weren’t terrible. After Nassau the trail to Kinderhook was much easier (aka flatter). We didn’t go all the way to Kinderhook but I’m looking forward to that another day. Beautiful trail.

Sue Grossman Still River Greenway

clean and well maintained.

June, 2021 by pkodance

Easy access and very flat and straight. Nice trail to cycle for couples and families.

Ashuwillticook Rail Trail

My home town trail is the best we have ridden yet!

June, 2021 by jsolon3680

This beautiful trail runs about 12.5 miles up to Adams, along wetlands, lakes and river! Wildlife abundant! So excited that is it being expanded!

Albany-Hudson Electric Trail

Beautiful Trail through wetlands and farmland, with abundant wildlife!

June, 2021 by jsolon3680

Rode the 25 mile stretch (50 miles RT) between Nasau Lake and Hudson. Nicely maintained and signed trail. Some stretches sharing the road, but in most cases, very easy to navigate! Many historical markers throughout that explain the rich history of this line and area!

Harlem Valley Rail Trail

Millerton to Taconic

June, 2021 by rmjm2squier

We finished this part of trail on June 18. All paved. The newest section had interesting concrete panels for bridge decks. Good mix of open and wooded areas helpful on 80 degree day. Great Scenery. Very flat. Would suggest some added signage inside state park where road is used. Also at north end of park no signage to indicate how to get to Hillsdale section.

Zim Smith Mid-County Trail

GREAT RIDE

June, 2021 by gtmskier

Rode today with my wife and adult son. Beautiful day, and trail is excellent.

Find Nearby City trails

Accordion

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 30,000 miles of trail maps and more!

Register with Google

Register with Apple

OR