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Best Hiking Trails near Westborough, Massachusetts
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Hiking Trails (820)
Parks & Forests (22)
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Rank
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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
Mount Watatic Loop via Wapack Trail
★
★
★
★
★
EASY
4.1
mi
3
Beauregard Lot via Half Way House Road
★
★
★
★
★
MODERATE
5.0
mi
4
Horse Caves Loop via NET/M&M Trail and Robert Frost Trail
★
★
★
★
★
EASY
3.4
mi
5
Great Blue Hill via Summit Road
★
★
★
★
★
EASY
2.0
mi
6
Beauregard Lot via Dublin Trail / Monadnock-Sunapee Greenway
★
★
★
★
★
MODERATE
4.3
mi
7
Sawyer Lot Loop via White Dot Trail
★
★
★
★
★
MODERATE
5.4
mi
8
A hike through Mt. Holyoke Range and Skinner State Parks
★
★
★
★
★
MODERATE
7.4
mi
9
Breakneck Ledge Loop via North Skyline Trail
★
★
★
★
★
EASY
3.5
mi
10
Pack Monadnock Mountain via Raymond Trail
★
★
★
★
★
EASY
2.8
mi
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