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Best Hiking Trails near Winchester, Massachusetts
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Hiking Trails (751)
Parks & Forests (24)
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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
Great Blue Hill via Summit Road
★
★
★
★
★
EASY
2.0
mi
4
Breakneck Ledge Loop via North Skyline Trail
★
★
★
★
★
EASY
3.5
mi
5
Pack Monadnock Mountain via Raymond Trail
★
★
★
★
★
EASY
2.8
mi
6
South Mount Pawtuckaway via Mountain Trail
★
★
★
★
★
MODERATE
5.5
mi
7
Babson Farms Quarry
★
★
★
★
★
EASY
1.4
mi
8
Puds Pond Loop via Pond Walk
★
★
★
★
★
EASY
2.9
mi
9
Wachusett Mountain Loop via Old Indian Trail and Semuhenna Trail
★
★
★
★
★
EASY
3.6
mi
10
Lake Cochichewick Loop via Edgewood Farm Trail and Stevens Trail
★
★
★
★
★
EASY
2.5
mi
1
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76
Cape Cod National Seashore
Leominster State Forest
Boston Harbor Islands National Recreation Area
Harold Parker State Forest
James L. Goodwin State Forest
Douglas State Forest
Borderland State Park
Lowell Dracut Tyngsborough State Forest
Great Meadows National Wildlife Refuge
Great Meadows National Wildlife Refuge
Mashamoquet Brook State Park
Roxbury Heritage State Park
Airline State Park Trail (Northern Section)
Roxbury Heritage State Park
Bradley Palmer State Park
Killingly Pond State Park Reserve
Massasoit National Wildlife Refuge
Massasoit National Wildlife Refuge
Natchaug State Forest
Old Furnace State Park
Pilgrim Memorial State Park
Quaddick State Park
Roger Williams National Monument
Ross Pond State Park