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Best Hiking Trails near Cheshire, Massachusetts
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Hiking Trails (560)
Parks & Forests (27)
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Time
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Difficulty
Length
Length
1-20 miles
Activity
All
Hiking
Offroading
1
Horse Caves Loop via NET/M&M Trail and Robert Frost Trail
★
★
★
★
★
EASY
3.4
mi
2
A hike through Mt. Holyoke Range and Skinner State Parks
★
★
★
★
★
MODERATE
7.4
mi
3
Mt Washington State Forest via Mt. Fissell Trail
★
★
★
★
★
EASY
3.1
mi
4
Metacomet Trail
★
★
EASY
4.9
mi
5
Vista Loop via Overlook Trail and Appalachian Trail
★
★
★
★
★
EASY
2.6
mi
6
Devils Garden via NET/M&M Trail
★
★
★
★
★
EASY
4.7
mi
7
Race Brook Trail to ymca camp
★
★
★
★
★
MODERATE
5.1
mi
8
Aldrich Lake Loop via Roller Coaster
★
★
★
★
★
EASY
2.6
mi
9
Undermountain Trail and Appalachian Trail Loop
★
★
★
★
★
DIFFICULT
8.2
mi
10
Island Spouter via Geyser Loop Road
★
★
★
★
★
EASY
3.2
mi
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Green Mountain National Forest Hiking Trails
Green Mountain National Forest Hiking Trails
Indian Head Wilderness Hiking Trails
Windham-Blackhead Range Wilderness Hiking Trails
Lye Brook Wilderness Hiking Trails
Glastenbury Wilderness Hiking Trails
Joseph Allen Skinner State Park Hiking Trails
American Legion State Forest Hiking Trails
Taconic State Park - Copake Falls Area Hiking Trails
Taconic State Park - Rudd Pond Area Hiking Trails
Bash Bish Falls State Park Hiking Trails
Grafton Lakes State Park Hiking Trails
Federated Women's Club State Forest Hiking Trails
Clarksburg State Park Hiking Trails
Ogden Mills and Ruth Livingston Mills State Park Hiking Trails
Dennis Hill State Park Hiking Trails
Erving State Forest Hiking Trails
George D. Aiken Wilderness Hiking Trails
Bash Bish Falls State Park Hiking Trails
Bristol Beach State Park Hiking Trails
Connecticut River Greenway State Park Hiking Trails
Connecticut River Greenway State Park Hiking Trails
Connecticut River Greenway State Park Hiking Trails
Enders State Forest Hiking Trails
Airline State Park Trail (Northern Section) Hiking Trails
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John A. Minetto State Park Hiking Trails