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Best Hiking Trails near Winchendon, Massachusetts
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Hiking Trails (790)
Parks & Forests (21)
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Rank
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Time
Stars
Difficulty
Length
Length
1-20 miles
Activity
All
Hiking
Offroading
1
Mount Watatic Loop via Wapack Trail
★
★
★
★
★
EASY
4.1
mi
2
Beauregard Lot via Half Way House Road
★
★
★
★
★
MODERATE
5.0
mi
3
Horse Caves Loop via NET/M&M Trail and Robert Frost Trail
★
★
★
★
★
EASY
3.4
mi
4
Beauregard Lot via Dublin Trail / Monadnock-Sunapee Greenway
★
★
★
★
★
MODERATE
4.3
mi
5
A hike through Mt. Holyoke Range and Skinner State Parks
★
★
★
★
★
MODERATE
7.4
mi
6
Sawyer Lot Loop via White Dot Trail
★
★
★
★
★
MODERATE
5.4
mi
7
Pack Monadnock Mountain via Raymond Trail
★
★
★
★
★
EASY
2.8
mi
8
Beauregard Lot via Pumpelly Trail
★
★
★
★
★
MODERATE
4.0
mi
9
Mt Monadnock State Park Campground via Birchtoft Trail
★
★
★
★
★
MODERATE
6.6
mi
10
Wachusett Mountain Loop via Old Indian Trail and Semuhenna Trail
★
★
★
★
★
EASY
3.6
mi
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79
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