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Best Hiking Trails near Southborough, Massachusetts
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Hiking Trails (798)
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
Great Blue Hill via Summit Road
★
★
★
★
★
EASY
2.0
mi
5
Sawyer Lot Loop via White Dot Trail
★
★
★
★
★
MODERATE
5.4
mi
6
Pack Monadnock Mountain via Raymond Trail
★
★
★
★
★
EASY
2.8
mi
7
Breakneck Ledge Loop via North Skyline Trail
★
★
★
★
★
EASY
3.5
mi
8
Mt Monadnock State Park Campground via Birchtoft Trail
★
★
★
★
★
MODERATE
6.6
mi
9
Puds Pond Loop via Pond Walk
★
★
★
★
★
EASY
2.9
mi
10
Lake Cochichewick Loop via Edgewood Farm Trail and Stevens Trail
★
★
★
★
★
EASY
2.5
mi
1
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Green Mountain National Forest
Green Mountain National Forest
Leominster State Forest
Boston Harbor Islands National Recreation Area
Harold Parker State Forest
Douglas State Forest
James L. Goodwin State Forest
Borderland State Park
Gay City State Park
Federated Women's Club State Forest
Great Meadows National Wildlife Refuge
Great Meadows National Wildlife Refuge
Erving State Forest
Airline State Park Trail (Southern Section)
Roger Williams National Monument
Bradley Palmer State Park
Colt State Park
Haines Memorial State Park
Hopeville Pond State Park
Hop River State Park Trail
Killingly Pond State Park Reserve
Airline State Park Trail (Northern Section)