Hiking Trails in Massachusetts

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

The Knob at Quissett Harbor Trail

The Knob at Quissett Harbor Trail

Falmouth, Massachusetts

1.4 km18 mgain
EasyLoop
The Ledge Loop

The Ledge Loop

Assonet, Massachusetts

5.3 km149 mgain
EasyLoop
The Willowbrook Farm Trail

The Willowbrook Farm Trail

Pembroke, Massachusetts

4.2 km92 mgain
EasyLoop
Thomas Road Loop

Thomas Road Loop

Boxford, Massachusetts

5.5 km60 mgain
EasyLoop
Thompson Family Forever Wild Preserve Loop Trail [PRIVATE PROPERTY]

Thompson Family Forever Wild Preserve Loop Trail [PRIVATE PROPERTY]

Southbridge, Massachusetts

10.0 km297 mgain
EasyLoop
Thompson Mountain Loop

Thompson Mountain Loop

Gloucester, Massachusetts

2.3 km60 mgain
ModerateLoop
Tiasquam Valley to Wiskosim’s Rock

Tiasquam Valley to Wiskosim’s Rock

Chilmark, Massachusetts

6.0 km179 mgain
ModerateOut & Back
Tidmarsh Wildlife Sanctuary

Tidmarsh Wildlife Sanctuary

Plymouth, Massachusetts

2.3 km50 mgain
EasyLoop
Tipping Rock via Monson, Nixon, Thirty Rd, and Legion Trails

Tipping Rock via Monson, Nixon, Thirty Rd, and Legion Trails

Sudbury, Massachusetts

3.5 km87 mgain
ModerateLoop
Tippling Rock & Fords Folly

Tippling Rock & Fords Folly

Sudbury, Massachusetts

6.4 km184 mgain
EasyOut & Back
Tippling Rock to Bay Circuit Trail

Tippling Rock to Bay Circuit Trail

Sudbury, Massachusetts

2.3 km67 mgain
ModerateOut & Back
Tisbury Great Pond Trail

Tisbury Great Pond Trail

Edgartown, Massachusetts

4.0 km49 mgain
ModerateOut & Back
Tisbury Meadow Preserve Loop

Tisbury Meadow Preserve Loop

Vineyard Haven, Massachusetts

3.9 km91 mgain
EasyLoop
Tom Leary Trail

Tom Leary Trail

Wilbraham, Massachusetts

4.8 km269 mgain
ModerateLoop
Tower Hill Botanic Garden Loop Trail

Tower Hill Botanic Garden Loop Trail

Boylston, Massachusetts

1.6 km48 mgain
EasyLoop
Tower Trail to Chickering Lake

Tower Trail to Chickering Lake

Medfield, Massachusetts

1.9 km74 mgain
EasyLoop
Towle Inner and Outer Loop

Towle Inner and Outer Loop

Carlisle, Massachusetts

3.5 km73 mgain
EasyLoop
Towle Inner Loop

Towle Inner Loop

Carlisle, Massachusetts

1.4 km30 mgain
EasyLoop
Town Forest Red and Yellow Loop

Town Forest Red and Yellow Loop

Acton, Massachusetts

1.8 km33 mgain
EasyLoop
Town Forest Tour Trail

Town Forest Tour Trail

Buzzards Bay, Massachusetts

2.7 km54 mgain
ModerateLoop
Town Forest Yellow and Blue Loop

Town Forest Yellow and Blue Loop

Harvard, Massachusetts

1.3 km47 mgain
ModerateLoop
Townsend Quarries Loop

Townsend Quarries Loop

Townsend, Massachusetts

4.8 km198 mgain
ModerateLoop
Trade Wind Fields and Farm Pond Preserves Loop Trail

Trade Wind Fields and Farm Pond Preserves Loop Trail

Oak Bluffs, Massachusetts

4.8 km100 mgain
EasyLoop
Trail of Tears Loop via Scott Rock, Lookout, and North Ridge Trail

Trail of Tears Loop via Scott Rock, Lookout, and North Ridge Trail

West Barnstable, Massachusetts

9.0 km167 mgain
ModerateLoop
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