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Best trails in Pittsfield

658 Reviews
Looking for a great trail near Pittsfield, Massachusetts? AllTrails has 13 great hiking trails, trail running trails, forest trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Mount Riga State Park or Bash Bish Falls State Park, we've got you covered. You'll also find some great local park options, like Mount Greylock State Reservation or Mount Everett State Reservation. Ready for some activity? There are 8 moderate trails in Pittsfield ranging from 1.5 to 6.7 miles and from 1,128 to 2,194 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Pittsfield
Top trails (13)
#1 - Shaker Mountain Loop via Shaker Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(159)
Length: 5.4 mi • Est. 2 h 54 m
Shaker Mountain, 1,835 feet (559 m), is a prominent peak in the Taconic Mountains of western Massachusetts. The mountain is located in Pittsfield State Forest and is named after the nearby Hancock Shaker Village, a former Shaker religious colony and now a historic site. The summit is wooded and is traversed by the Shaker Trail, a loop trail that begins at the historic site. The mountain is wooded with northern hardwood tree species. Wonderful ruins and stone walls to view. Very peaceful location and the trails are not blazed but clearly marked. This hike is moderate to strenuous bring your hiking boots and walking stick. Show more
#2 - Ashuwillticook Rail Trail
Pittsfield, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(170)
Length: 10.8 mi • Est. 4 h 24 m
#3 - Canoe Meadows Wildlife Sanctuary Trail
Canoe Meadows Wildlife Sanctuary
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(65)
Length: 2.8 mi • Est. 1 h 9 m
#4 - Twin Pond via Taconic Crest Trail to Taconic Skyline Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(53)
Length: 3.5 mi • Est. 1 h 54 m
#5 - Holy Mount via Shaker Trail
Pittsfield State Forest
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Length: 6.7 mi • Est. 3 h 36 m
Five miles west of Pittsfield. Constructed and maintained by the Boy Scouts of America, this circuit travels wooded, stream, and hilltop sites key to a 19th-cintury Shaker society.Show more
#6 - Berry Pond Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(21)
Length: 1.5 mi • Est. 41 m
#7 - Mahanna Cobble
Pittsfield, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow Star(21)
Length: 2.7 mi • Est. 1 h 4 m
This is a pleasant hike up to Mahanna Cobble. The first 10 minutes will get your heart rate going, but then it’s steady up the rest of the way to a beautiful view at George’s Bench.Show more
#8 - Wild Acres Park
Wild Acres Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(35)
Length: 1.2 mi • Est. 31 m
#9 - Turner Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(20)
Length: 3.8 mi • Est. 2 h 9 m
#10 - Shaker Mountain (Short Option)
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(23)
Length: 3.3 mi • Est. 1 h 48 m
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