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Best Hiking Trails near Monterey, Massachusetts
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Hiking Trails (608)
Parks & Forests (25)
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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
Notch Lake via Devil's Path
★
★
★
★
★
DIFFICULT
11.4
mi
6
Horse Caves Loop via NET/M&M Trail and Robert Frost Trail
★
★
★
★
★
EASY
3.4
mi
7
~2.3-mi loop hike in Doctor Francis Giuffrida Park
★
★
★
★
★
EASY
2.3
mi
8
Blackhead Loop via Black Dome Range Trail
★
★
★
★
★
MODERATE
4.8
mi
9
Plateau Mountain via Devil's Path
★
★
★
★
★
MODERATE
3.9
mi
10
A hike through Mt. Holyoke Range and Skinner State Parks
★
★
★
★
★
MODERATE
7.4
mi
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Green Mountain National Forest
Green Mountain National Forest
Hudson Highlands State Park
Indian Head Wilderness
Minnewaska State Park Preserve
Windham-Blackhead Range Wilderness
Clarence Fahnestock Memorial State Park
Wonder Lake State Park
Bash Bish Falls State Park
Taconic State Park - Rudd Pond Area
Taconic State Park - Copake Falls Area
Airline State Park Trail (Southern Section)
Clarksburg State Park
Federated Women's Club State Forest
Ogden Mills and Ruth Livingston Mills State Park
Franny Reese State Park
Dart Island State Park
James Baird State Park
Margaret Lewis Norrie State Park
Connecticut River Greenway State Park
Bash Bish Falls State Park
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Cherry Plain State Park
George D. Aiken Wilderness