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Best Hiking Trails near Boylston, Massachusetts
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Hiking Trails (837)
Parks & Forests (18)
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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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Green Mountain National Forest
Green Mountain National Forest
Boston Harbor Islands National Recreation Area
Borderland State Park
Douglas State Forest
Gay City State Park
Erving State Forest
Great Meadows National Wildlife Refuge
Great Meadows National Wildlife Refuge
Airline State Park Trail (Southern Section)
Federated Women's Club State Forest
Roger Williams National Monument
Bradley Palmer State Park
Colt State Park
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Airline State Park Trail (Northern Section)