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Best Hiking Trails near Westport, Massachusetts
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Hiking Trails (303)
Parks & Forests (22)
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Time
Stars
Difficulty
Length
Length
1-20 miles
Activity
All
Hiking
Offroading
1
Hancock Hill via North Skyline Trail
★
★
★
★
★
EASY
2.9
mi
2
Great Blue Hill via Summit Road
★
★
★
★
★
EASY
2.0
mi
3
Breakneck Ledge Loop via North Skyline Trail
★
★
★
★
★
EASY
3.5
mi
4
Puds Pond Loop via Pond Walk
★
★
★
★
★
EASY
2.9
mi
5
Boyce Hill Loop via Tucker Hill Path and Dark Hollow Path
★
★
★
★
★
MODERATE
5.7
mi
6
Hancock Hill Loop via North Skyline Trail
★
★
★
★
★
EASY
3.5
mi
7
Tucker Hill Loop
★
★
★
★
★
MODERATE
6.6
mi
8
Easy 1.9 mi:Trailside Museum via Summit Rd/N Skyline Trail
★
★
★
★
EASY
1.9
mi
9
Breeze Hill Loop
★
★
★
★
DIFFICULT
9.6
mi
10
Flagstaff Hill
★
★
★
MODERATE
6.8
mi
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