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Best trails in Pittsfield

515 Reviews
Looking for a great trail near Pittsfield, Massachusetts? AllTrails has 11 great hiking trails, walking 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 6 moderate trails in Pittsfield ranging from 1.5 to 6.7 miles and from 1,181 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 (11)
#1 - Shaker Mountain Loop via Shaker Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(138)
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 ShaShow more
#2 - Ashuwillticook Rail Trail
Pittsfield, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(143)
Length: 10.8 mi • Est. 4 h 24 m
Note: There is a temporary closure of the northern section due to construction.Show more
#3 - Twin Pond via Taconic Crest Trail to Taconic Skyline Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(49)
Length: 3.5 mi • Est. 1 h 54 m
Twin Pond via Taconic Crest Trail to Taconic Skyline Trail is a 3.5 mile moderately trafficked loop trail located near Pittsfield, Massachusetts that features a lake and is rated as moderate. The traiShow more
#4 - Holy Mount via Shaker Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(34)
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
#5 - Canoe Meadows Wildlife Sanctuary Trail
Canoe Meadows Wildlife Sanctuary
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(55)
Length: 2.8 mi • Est. 1 h 9 m
Canoe Meadows Wildlife Sanctuary Trail is a 2.8 mile moderately trafficked loop trail located near Pittsfield, Massachusetts that offers the chance to see wildlife and is good for all skill levels. ThShow more
#6 - Wild Acres Park
Wild Acres Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(28)
Length: 1.2 mi • Est. 31 m
Wild Acres Park is a 1.2 mile lightly trafficked loop trail located near Pittsfield, Massachusetts that features a lake and is good for all skill levels. The trail is primarily used for walking, runniShow more
#7 - Berry Pond Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(14)
Length: 1.5 mi • Est. 41 m
Berry Pond Trail is a 1.5 mile moderately trafficked loop trail located near Pittsfield, Massachusetts that features a lake and is rated as moderate. The trail is primarily used for hiking and walkingShow more
#8 - Shaker Mountain (Short Option)
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(25)
Length: 3.3 mi • Est. 1 h 48 m
Shaker Mountain (Short Option) is a 3.3 mile moderately trafficked out and back trail located near Pittsfield, Massachusetts that features a lake and is rated as moderate. The trail is primarily used Show more
#9 - Turner Trail
Pittsfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(14)
Length: 3.8 mi • Est. 2 h 9 m
Turner Trail is a 3.8 mile moderately trafficked out and back trail located near Pittsfield, Massachusetts that features beautiful wild flowers. The trail is rated as moderate and is primarily used foShow more
#10 - Brickhouse Mountain Trail
Pittsfield, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray Star(6)
Length: 4 mi • Est. 1 h 50 m
Brickhouse Mountain Trail is a 4 mile moderately trafficked loop trail located near Pittsfield, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail is primarShow more
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