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Best Hiking Trails near Pepperell, Massachusetts
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Hiking Trails (923)
Parks & Forests (16)
Sort
Rank
▼
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
Great Blue Hill via Summit Road
★
★
★
★
★
EASY
2.0
mi
5
Beauregard Lot via Dublin Trail / Monadnock-Sunapee Greenway
★
★
★
★
★
MODERATE
4.3
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
Breakneck Ledge Loop via North Skyline Trail
★
★
★
★
★
EASY
3.5
mi
9
Beauregard Lot via Pumpelly Trail
★
★
★
★
★
MODERATE
4.0
mi
10
South Mount Pawtuckaway via Mountain Trail
★
★
★
★
★
MODERATE
5.5
mi
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Green Mountain National Forest
Green Mountain National Forest
Mount Holyoke Range State Park
Mount Holyoke Range State Park
Leominster State Forest
Harold Parker State Forest
Boston Harbor Islands National Recreation Area
Borderland State Park
Douglas State Forest
Lowell Dracut Tyngsborough State Forest
Great Meadows National Wildlife Refuge
Erving State Forest
Federated Women's Club State Forest
Great Meadows National Wildlife Refuge
Airline State Park Trail (Northern Section)
Bradley Palmer State Park