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Best Hiking Trails near Windsor, Massachusetts
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Hiking Trails (571)
Parks & Forests (26)
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Time
Stars
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
stake Loop via and Metacomet Trail
★
★
★
★
★
EASY
4.1
mi
4
Mt Washington State Forest via Mt. Fissell Trail
★
★
★
★
★
EASY
3.1
mi
5
Metacomet Trail
★
★
EASY
4.9
mi
6
Race Brook Trail to ymca camp
★
★
★
★
★
MODERATE
5.1
mi
7
Vista Loop via Overlook Trail and Appalachian Trail
★
★
★
★
★
EASY
2.6
mi
8
Devils Garden via NET/M&M Trail
★
★
★
★
★
EASY
4.7
mi
9
Aldrich Lake Loop via Roller Coaster
★
★
★
★
★
EASY
2.6
mi
10
Undermountain Trail and Appalachian Trail Loop
★
★
★
★
★
DIFFICULT
8.2
mi
1
2
3
4
5
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Green Mountain National Forest Hiking Trails
Green Mountain National Forest Hiking Trails
Lye Brook Wilderness Hiking Trails
Glastenbury Wilderness Hiking Trails
James L. Goodwin State Forest Hiking Trails
Taconic State Park - Copake Falls Area Hiking Trails
Taconic State Park - Rudd Pond Area Hiking Trails
Grafton Lakes State Park Hiking Trails
American Legion State Forest Hiking Trails
Bash Bish Falls State Park Hiking Trails
Ogden Mills and Ruth Livingston Mills State Park Hiking Trails
Erving State Forest Hiking Trails
Clarksburg State Park Hiking Trails
Federated Women's Club State Forest Hiking Trails
George D. Aiken Wilderness Hiking Trails
Bash Bish Falls State Park Hiking Trails
Bristol Beach State Park Hiking Trails
Cherry Plain 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
Hop River State Park Trail Hiking Trails
Hudson River Islands State Park Hiking Trails
Margaret Lewis Norrie State Park Hiking Trails