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Best Hiking Trails near Winthrop, Massachusetts
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Hiking Trails (646)
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
Great Blue Hill via Summit Road
★
★
★
★
★
EASY
2.0
mi
3
Breakneck Ledge Loop via North Skyline Trail
★
★
★
★
★
EASY
3.5
mi
4
Wachusett Mountain Loop via Bicentennial Trail
★
★
★
★
★
EASY
1.7
mi
5
Babson Farms Quarry
★
★
★
★
★
EASY
1.4
mi
6
Puds Pond Loop via Pond Walk
★
★
★
★
★
EASY
2.9
mi
7
Lake Cochichewick Loop via Edgewood Farm Trail and Stevens Trail
★
★
★
★
★
EASY
2.5
mi
8
Melrose Rock Loop via Rock Circuit Trail
★
★
★
★
★
EASY
4.5
mi
9
Quarry Spring Loop via Quarry Road and Skyline Trail
★
★
★
EASY
1.2
mi
10
Bellevue Pond via Skyline Trail
★
★
★
★
★
EASY
1.3
mi
1
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65
Cape Cod National Seashore
Leominster State Forest
Boston Harbor Islands National Recreation Area
Harold Parker State Forest
Borderland State Park
Douglas State Forest
Lowell Dracut Tyngsborough State Forest
Nickerson State Park
Great Meadows National Wildlife Refuge
Great Meadows National Wildlife Refuge
Pilgrim Memorial State Park
Airline State Park Trail (Northern Section)
Roger Williams National Monument
Bradley Palmer State Park
Colt State Park
Haines Memorial State Park
Killingly Pond State Park Reserve
Massasoit National Wildlife Refuge
Massasoit National Wildlife Refuge
Moosup Valley State Park Trail
Natchaug State Forest
Old Furnace State Park