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Hiking Trails in Massachusetts

Discover 1,218 routes with difficulty, elevation, and trail stats. Built for quickly narrowing down the right hike.

Tiasquam Valley to Wiskosim’s Rock
Trail

Tiasquam Valley to Wiskosim’s Rock

Chilmark, Massachusetts

3.7 mi587 ftgain
ModerateOut & Back
Tidmarsh Wildlife Sanctuary
Trail

Tidmarsh Wildlife Sanctuary

Plymouth, Massachusetts

1.4 mi164 ftgain
EasyLoop
Tipping Rock via Monson, Nixon, Thirty Rd, and Legion Trails
Trail

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

Sudbury, Massachusetts

2.2 mi285 ftgain
ModerateLoop
Tippling Rock & Fords Folly
Trail

Tippling Rock & Fords Folly

Sudbury, Massachusetts

4.0 mi604 ftgain
ModerateOut & Back
Tippling Rock to Bay Circuit Trail
Trail

Tippling Rock to Bay Circuit Trail

Sudbury, Massachusetts

1.4 mi220 ftgain
ModerateOut & Back
Tisbury Great Pond Trail
Trail

Tisbury Great Pond Trail

Edgartown, Massachusetts

2.5 mi161 ftgain
ModerateOut & Back
Tisbury Meadow Preserve Loop
Trail

Tisbury Meadow Preserve Loop

Vineyard Haven, Massachusetts

2.4 mi299 ftgain
EasyLoop
Tom Leary Trail
Trail

Tom Leary Trail

Wilbraham, Massachusetts

3.0 mi883 ftgain
ModerateLoop
Tower Hill Botanic Garden Loop Trail
Trail

Tower Hill Botanic Garden Loop Trail

Boylston, Massachusetts

1.0 mi157 ftgain
EasyLoop
Tower Trail to Chickering Lake
Trail

Tower Trail to Chickering Lake

Medfield, Massachusetts

1.2 mi243 ftgain
EasyLoop
Towle Inner and Outer Loop
Trail

Towle Inner and Outer Loop

Carlisle, Massachusetts

2.2 mi240 ftgain
EasyLoop
Towle Inner Loop
Trail

Towle Inner Loop

Carlisle, Massachusetts

0.9 mi98 ftgain
EasyLoop
Town Forest Red and Yellow Loop
Trail

Town Forest Red and Yellow Loop

Acton, Massachusetts

1.1 mi108 ftgain
EasyLoop
Town Forest Tour Trail
Trail

Town Forest Tour Trail

Buzzards Bay, Massachusetts

1.7 mi177 ftgain
ModerateLoop
Town Forest Yellow and Blue Loop
Trail

Town Forest Yellow and Blue Loop

Harvard, Massachusetts

0.8 mi154 ftgain
ModerateLoop
Townsend Quarries Loop
Trail

Townsend Quarries Loop

Townsend, Massachusetts

3.0 mi650 ftgain
ModerateLoop
Trade Wind Fields and Farm Pond Preserves Loop Trail
Trail

Trade Wind Fields and Farm Pond Preserves Loop Trail

Oak Bluffs, Massachusetts

3.0 mi328 ftgain
EasyLoop
Trail of Tears Loop via Scott Rock, Lookout, and North Ridge Trail
Trail

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

West Barnstable, Massachusetts

5.6 mi548 ftgain
ModerateLoop
Tri-Community Greenway
Trail

Tri-Community Greenway

Stoneham, Massachusetts

12.7 mi1,010 ftgain
ExpertOut & Back
Tri-Point and Midstate Loop
Trail

Tri-Point and Midstate Loop

Douglas, Massachusetts

10.4 mi1,335 ftgain
DifficultLoop
Tri-State Marker
Trail

Tri-State Marker

Douglas, Massachusetts

5.4 mi686 ftgain
ModerateLoop
Tri-Tow, Otter Alley, Winterbury Way Loop
Trail

Tri-Tow, Otter Alley, Winterbury Way Loop

Sudbury, Massachusetts

3.7 mi394 ftgain
ModerateLoop
Tri-Town, Harrys Way and Hill Trail Loop
Trail

Tri-Town, Harrys Way and Hill Trail Loop

Sudbury, Massachusetts

4.8 mi358 ftgain
EasyLoop
Triphammer Loop
Trail

Triphammer Loop

Hingham, Massachusetts

1.5 mi279 ftgain
EasyLoop
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