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Best Hiking Trails near Pittsfield, Massachusetts
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Hiking Trails (621)
Parks & Forests (28)
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Time
Stars
Difficulty
Length
Length
1-20 miles
Activity
All
Hiking
Offroading
1
Camp Steel overlook Loop via Black Dome Range Trail
★
★
★
★
★
MODERATE
6.6
mi
2
Sugarloaf Mountain overlook Loop via Pecoy Notch Trail and Devil's Path
★
★
★
★
★
MODERATE
6.3
mi
3
Windham High Peak via Escarpment Trail
★
★
★
★
★
MODERATE
6.4
mi
4
Sherman's Lookout via Prediger Road Trail Head
★
★
★
★
★
MODERATE
6.1
mi
5
Horse Caves Loop via NET/M&M Trail and Robert Frost Trail
★
★
★
★
★
EASY
3.4
mi
6
Notch Lake via Devil's Path
★
★
★
★
★
DIFFICULT
11.4
mi
7
Blackhead Loop via Black Dome Range Trail
★
★
★
★
★
MODERATE
4.8
mi
8
A hike through Mt. Holyoke Range and Skinner State Parks
★
★
★
★
★
MODERATE
7.4
mi
9
Echo Lake
★
★
★
★
EASY
3.8
mi
10
stake Loop via and Metacomet Trail
★
★
★
★
★
EASY
4.1
mi
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63
Green Mountain National Forest
Green Mountain National Forest
Minnewaska State Park Preserve
Indian Head Wilderness
Windham-Blackhead Range Wilderness
Hunter-West Kill Wilderness
Lye Brook Wilderness
Grafton Lakes State Park
Bash Bish Falls State Park
Taconic State Park - Copake Falls Area
Taconic State Park - Rudd Pond Area
American Legion State Forest
Ogden Mills and Ruth Livingston Mills State Park
Erving State Forest
Clarksburg State Park
Dennis Hill State Park
Horse Guard State Park Scenic Reserve
Hop River State Park Trail
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Enders State Forest
George D. Aiken Wilderness
Cherry Plain State Park
Haystack Mountain State Park
Connecticut River Greenway State Park
Hudson River Islands State Park
Bash Bish Falls State Park
Margaret Lewis Norrie State Park