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Best Hiking Trails near Great Barrington, Massachusetts
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Hiking Trails (644)
Parks & Forests (26)
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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
Devil's Acre spring Loop via Spruceton Horse Trail
★
★
★
★
★
DIFFICULT
9.1
mi
5
Hunter Mountain via Becker Hollow Trail
★
★
★
★
★
MODERATE
4.6
mi
6
Sherman's Lookout via Prediger Road Trail Head
★
★
★
★
★
MODERATE
6.1
mi
7
Horse Caves Loop via NET/M&M Trail and Robert Frost Trail
★
★
★
★
★
EASY
3.4
mi
8
Notch Lake via Devil's Path
★
★
★
★
★
DIFFICULT
11.4
mi
9
Plateau Mountain via Devil's Path
★
★
★
★
★
MODERATE
3.9
mi
10
Blackhead Loop via Black Dome Range Trail
★
★
★
★
★
MODERATE
4.8
mi
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Green Mountain National Forest
Green Mountain National Forest
Hudson Highlands State Park
Slide Mountain Wilderness
Indian Head Wilderness
Minnewaska State Park Preserve
Windham-Blackhead Range Wilderness
Clarence Fahnestock Memorial State Park
Hunter-West Kill Wilderness
Taconic State Park - Copake Falls Area
Taconic State Park - Rudd Pond Area
Wonder Lake State Park
Bash Bish Falls State Park
Airline State Park Trail (Southern Section)
Ogden Mills and Ruth Livingston Mills State Park
George D. Aiken Wilderness
Franny Reese State Park
James Baird State Park
Margaret Lewis Norrie State Park
Farmington Canal Line State Park Trail
Bash Bish Falls State Park
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Cherry Plain State Park
Highland Lakes State Park