Pittsfield, MA Fishing Trails and Maps

1021 Reviews

Looking for the best Fishing trails around Pittsfield?

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

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Activities
Length
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17 Results
Activities
Length
Surfaces
Type

Ashuwillticook Rail Trail

13.9 mi
State: MA
Asphalt

Ballston Veterans Bike Path

3.5 mi
State: NY
Asphalt

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Champlain Canalway Trail: Schuylerville

2 mi
State: NY
Crushed Stone

Erie Canalway Trail

335.2 mi
State: NY
Asphalt, Concrete, Crushed Stone

Farmington Canal Heritage Trail

49.1 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Concrete, Crushed Stone

Manhan Rail Trail

9.5 mi
State: MA
Asphalt

Mass Central Rail Trail

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

Bog Meadow Brook Nature Trail

2 mi
State: NY
Ballast, Dirt

Champlain Canalway Trail: Saratoga

1.5 mi
State: NY
Crushed Stone, Dirt

Connecticut Riverwalk and Bikeway

7.8 mi
State: MA
Asphalt

Fort Hill Recreational Rail Trail

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

Hoosic River Greenway

2.5 mi
State: NY
Gravel

Bennington Rail Trail

1.65 mi
State: VT
Asphalt, Crushed Stone, Gravel

East Branch Trail (VT)

0.5 mi
State: VT
Gravel
Trail Image Trail Name States Length Surface Rating
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along a 13.7-mile paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through the Hoosic...
MA 13.9 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
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 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
Closure Notices: In Palmyra/Wayne County, a portion of the trail is closed between route 21 and Swift Landing Park. In Oneida-Verona, Oneida County, a bridge replacement is taking place at the corner...
NY 335.2 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 49.1 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, Concrete, 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 9.5 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. The Mass Central Rail Trail runs for 36.36 miles from...
MA 56.36 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
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 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 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 7.8 mi Asphalt
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
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
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
Running between downtown Bennington and the Northside Drive neighborhoods, the Bennington Rail Trail provides new opportunities for both recreation and active transportation. Following a former...
VT 1.65 mi Asphalt, Crushed Stone, Gravel
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

Recent Trail Reviews

Windsor Locks Canal State Park Trail

Nice Biking spot for a 10-ish mile ride

September, 2025 by mtheis.45

Had a great evening bike ride out at the Windsor Locks Canal trail earlier this month (Aug, '25). The trail is paved, and as others have mentioned, it is not super smooth in some areas where the tree roots are pushing the asphalt up but can be navigated pretty easily. I was riding my gravel bike setup with 42mm tires and was able to go quite fast - averaging 15mph on the ride so it really was not that beat up / bad.

The scenery on the river is very nice, and the canal on the other side was also fun - lots of wildlife to see. Would recommend if in the area!

Farmington Canal Heritage Trail

Rode the entire trail…

September, 2025 by willipar

Rode the entire Farmington Canal Heritage Trail as part of a 2 day ride from Northampton to New Haven. What a fabulous experience! So much variety and New England splendor packed into one journey. It was very interesting to see how each of the towns maintained the trail differently. Everything from the paving to the signage changed as you moved from one village to the next. What an amazing treasure!

Columbia Greenway Rail Trail

Beautifully Designed and Maintained

September, 2025 by willipar

A pleasure to ride!

Accordion

Fort Hill Recreational Rail Trail

We found this trail to be well maintained. Not as smooth as some rail trails, but smooth enough on our full suspension fat tire bikes. Hard tails may not enjoy as much. Nice scenery along the Connecticut river.

August, 2025 by jimthurber13

We found this trail to be well maintained. Not as smooth as some rail trails, but smooth enough on our full suspension fat tire bikes. Hard tails may not enjoy as much. Nice scenery along the Connecticut river.

Connecticut Riverwalk and Bikeway

River trail

August, 2025 by dawgpound99

Short for bike, nice views, benches and even a real train.

Mass Central Rail Trail

A Delightful Ride on The Norwottuck Section

August, 2025 by gettinlate

June 6th 2025
The Mrs and I rode this beautiful trail from North Hampton to just short of Belchertown, and back.
The weather was great and the trail is mostly shaded, so the ride was superb.
I'd have no objection to doing it again.

Ashuwillticook Rail Trail

Settle grade difference between start to finish. All paved smooth.No bugs.Crowded with walkers, skaters, and bikers.Windy in the afternoon.

August, 2025 by joy.olson15

Settle grade difference between start to finish. All paved smooth.No bugs.Crowded with walkers, skaters, and bikers.Windy in the afternoon.

Ashuelot Recreational Rail Trail

Nice ride.

August, 2025 by cgtaylor328

We started at the south end and rode ten miles before turning around. We would have gone further except it was getting late. The trail over all is in good condition. There hasn’t been a lot of rainfall recently so the trail was dry. We ride ebikes with four inch off road tires. On the day we rode the condition of the trail was good enough for most riders but we don’t recommend road bikes.

Harlem Valley Rail Trail

Rural trail with outstanding surface

August, 2025 by andrix

Parked at northern end just S of Orphan Farm Rd, NY; Trail surface is outstanding including numerous portions of elevated sections over wetlands. Did not see much in the way of wildlife. Quite rural with the 1st p potty 10 miles south; Turned back at Millerton; Shade 50% or so.

Ashuwillticook Rail Trail

Update to my 2024 review

August, 2025 by andrix

Update to my 8/2024 review: Remains a TOP trail; At northern end easy parking at the Adams Visitor Center; Saw many signs of beaver activity - dams and huts - but no beavers. The Appalachian Trail crosses at Church Road in Cheshire; At southern end I turn back at the Crane Ave. parking area as, in my opinion, there's not much of interest in the remaining mile or so.

Farmington Canal Heritage Trail

Needs Repaving

July, 2025 by dave36

Haven't ridden the trail since 2023. Rode from Cheshire down to New Haven, Saturday July 19th. Absolutely awful; entire section needs repaving and upkeep. Constant cracks in pavement and much debris on surface; plus glass and homeless down by the Wharf. Connecticut should take notice from Mass and NY on trail up keep. Both states's trail are far superior to CT. Also, difficult to navigate at trail end in New Haven if you don't know the city; poor signage.

Harlem Valley Rail Trail

great trail

July, 2025 by elj317

did trail 7 years ago. What a change!! Smooth all the way from Copake Falls to Wassaic!!!! Did 50 mile round trip then took a dip in the spring fed lake at Taconic Hills State park. Can walk to the lake from the trail head at copake falls. Also a nice state park with interesting sights. We stayed in Great Barrington , 10 miles from Copake Falls. Make sure you check out the Barrington Brewery. Great beer, great food.

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Accordion

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