Best Trails Near Pittsfield MA
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Best Trails Near Pittsfield MA

62
Trails
0 - 64 mi
Range
54
Hiking
34
Trail Running
56
Other activities
Pittsfield has 62 trails in the vicinity, including 54 hiking trails, 34 for trail running and 56 for other activities. These trails range from 0.1 to 64.2 miles in length. The longest trail in Pittsfield is Mount Greylock Challenge Ride a well-known trail measuring 64.2 miles in total length. The most popular trails are Pittsfield State Forest, Berry Pond Trail and New York Border Cruise Ride. Trails.com member JARED O. recently completed Berry Pond Trail.
Best Trails in Pittsfield 62 Results
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Although you are likely to find strawberries, blueberries, or raspberries along the trail ...
Climb it because it is there. When you summit Mount Greylock, you will be reaching the ...
This triangular loop route boasts a trifecta of water attractions— lovely cascades along ...
From the scenic Finerty Pond at the northern end of this section, past the wide expanse ...
Pretty Gore Pond is the destination of this day hike, which begins in Dalton. The pond ...
The main attraction of this day hike is the view of Cheshire and the Hoosic River valley ...
This out-and-back hike follows the Taconic Crest Trail, a quiet, long-distance hiking ...
Dublin's Run is a hiking trail in Pittsfield, Massachusetts. It is 0.5 miles long and ...
Deer Hill is a hiking trail in Pittsfield, Massachusetts. It is 1.2 miles long and begins ...
Whirlpool is a hiking trail in Pittsfield, Massachusetts. It is 0.4 miles long and begins ...
Beaver Tail Trail is a hiking trail in Pittsfield, Massachusetts. It is 0.7 miles long ...
Rotten Apple is a hiking trail in Pittsfield, Massachusetts. It is 0.5 miles long and ...
Mighty Maple is a hiking trail in Pittsfield, Massachusetts. It is 0.1 miles long and ...
Honey Bear is a hiking trail in Pittsfield, Massachusetts. It is 0.7 miles long and begins ...
Upper Rollercoaster is a hiking trail in Pittsfield, Massachusetts. It is 0.8 miles long ...
Fox Trot is a hiking trail in Pittsfield, Massachusetts. It is 0.2 miles long and begins ...
Ghost Ski Trail is a hiking trail in Pittsfield, Massachusetts. It is 0.5 miles long and ...
Shadow Ski Trail is a hiking trail in Pittsfield, Massachusetts. It is 0.6 miles long ...
Camp Winadu is a hiking trail in Pittsfield, Massachusetts. It is 0.2 miles long and begins ...
Whispering Pines is a hiking trail in Pittsfield, Massachusetts. It is 0.2 miles long ...
Neil's Niche is a hiking trail in Pittsfield, Massachusetts. It is 0.1 miles long and ...
Bear Claw is a hiking trail in Pittsfield, Massachusetts. It is 1.5 miles long and begins ...
Fuzzy Bunny is a hiking trail in Pittsfield, Massachusetts. It is 0.4 miles long and begins ...
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