Hiking Trails in Massachusetts

Discover 1,223 routes with difficulty, elevation, and trail stats. Built for quickly narrowing down the right hike.

Hammond Pond Reservation

Hammond Pond Reservation

Chestnut Hill, Massachusetts

2.6 km58 mgain
ModerateLoop
Hancock Hill and Hemenway Hill Loop

Hancock Hill and Hemenway Hill Loop

Milton, Massachusetts

2.3 km115 mgain
ModerateLoop
Hancock Hill and Jeffries Trail Loop

Hancock Hill and Jeffries Trail Loop

Milton, Massachusetts

2.6 km123 mgain
EasyLoop
Hapgood Wright Forest Loop

Hapgood Wright Forest Loop

Concord, Massachusetts

2.6 km74 mgain
EasyLoop
Harding Beach Point via Monomoy Nature Trail

Harding Beach Point via Monomoy Nature Trail

Chatham, Massachusetts

5.0 km86 mgain
EasyLoop
Harding's Beach Trail

Harding's Beach Trail

Chatham, Massachusetts

2.9 km34 mgain
ModerateLoop
Harold B. Clark Town Forest

Harold B. Clark Town Forest

Foxborough, Massachusetts

6.3 km149 mgain
EasyLoop
Harold Parker (East) and Salem Pond Loop

Harold Parker (East) and Salem Pond Loop

Andover, Massachusetts

6.6 km119 mgain
ModerateLoop
Harold Parker Loop Trail

Harold Parker Loop Trail

Andover, Massachusetts

26.7 km431 mgain
ModerateLoop
Harrington, Mountain House, Jack Frost, and High Meadow Trail Loop

Harrington, Mountain House, Jack Frost, and High Meadow Trail Loop

Princeton, Massachusetts

4.7 km289 mgain
EasyLoop
Hartland Hollow Road

Hartland Hollow Road

Granville, Massachusetts

6.0 km187 mgain
ModerateOut & Back
Harvard Forest Trail

Harvard Forest Trail

Petersham, Massachusetts

3.5 km129 mgain
EasyLoop
Harvard Pond Loop

Harvard Pond Loop

Petersham, Massachusetts

4.5 km178 mgain
EasyLoop
Hassanamesit Woods Trail

Hassanamesit Woods Trail

Grafton, Massachusetts

4.5 km122 mgain
EasyLoop
Hawkins Woods Loop

Hawkins Woods Loop

Plainville, Massachusetts

1.9 km33 mgain
EasyLoop
Hawley Trail

Hawley Trail

Charlemont, Massachusetts

18.3 km398 mgain
ModerateLoop
Hayden Woods Loop

Hayden Woods Loop

Lexington, Massachusetts

3.1 km54 mgain
EasyLoop
Haynes Reservoir to Blue Dot Loop

Haynes Reservoir to Blue Dot Loop

Leominster, Massachusetts

6.6 km227 mgain
ModerateLoop
Headwaters Conservation Area

Headwaters Conservation Area

Fall River, Massachusetts

2.6 km107 mgain
EasyLoop
Healthy Heart Trail Kendrick Pond Loop

Healthy Heart Trail Kendrick Pond Loop

Needham, Massachusetts

2.7 km60 mgain
EasyLoop
Heart Break Hill and Horse Loop

Heart Break Hill and Horse Loop

Brewster, Massachusetts

2.3 km41 mgain
EasyLoop
Heath Hen Meadow Pink, Purple, Blue Loop

Heath Hen Meadow Pink, Purple, Blue Loop

Stow, Massachusetts

2.7 km61 mgain
EasyLoop
Hedges Pond Loop

Hedges Pond Loop

Plymouth, Massachusetts

2.6 km66 mgain
EasyLoop
Helen Volkmann Trail

Helen Volkmann Trail

Boxborough, Massachusetts

1.8 km29 mgain
EasyOut & Back
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