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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.

Cheshire Harbor Trail to Mount Greylock
Trail

Cheshire Harbor Trail to Mount Greylock

Adams, Massachusetts

6.2 mi1,965 ftgain
DifficultOut & Back
Chesterfield Gorge Trail
Trail

Chesterfield Gorge Trail

West Chesterfield, Massachusetts

4.0 mi646 ftgain
ModerateOut & Back
Chestnut Hill Reservoir Trail
Trail

Chestnut Hill Reservoir Trail

Chestnut Hill, Massachusetts

1.6 mi240 ftgain
EasyLoop
Chestnut Hill via Warner Trail
Trail

Chestnut Hill via Warner Trail

Sharon, Massachusetts

2.1 mi269 ftgain
EasyLoop
Chestnut Run Path Loop
Trail

Chestnut Run Path Loop

Milton, Massachusetts

3.1 mi610 ftgain
ModerateLoop
Chestnut Run Path to Hancock Hill Summit
Trail

Chestnut Run Path to Hancock Hill Summit

Milton, Massachusetts

3.6 mi666 ftgain
ModerateOut & Back
Chestnut Trail to the Class of '98 Trail to the Appalachian Trail
Trail

Chestnut Trail to the Class of '98 Trail to the Appalachian Trail

Williamstown, Massachusetts

3.0 mi1,306 ftgain
DifficultOut & Back
Claire Birtz Wildlife Sanctuary
Trail

Claire Birtz Wildlife Sanctuary

Southbridge, Massachusetts

1.6 mi394 ftgain
ModerateLoop
Clam River Trail
Trail

Clam River Trail

Sandisfield, Massachusetts

3.6 mi909 ftgain
ModerateOut & Back
Clark's Cove Walk
Trail

Clark's Cove Walk

New Bedford, Massachusetts

1.8 mi246 ftgain
EasyOut & Back
Class of '33 Trail and down the old Williams College Ski Area
Trail

Class of '33 Trail and down the old Williams College Ski Area

Williamstown, Massachusetts

3.2 mi1,611 ftgain
DifficultLoop
Cleveland Pond Loop
Trail

Cleveland Pond Loop

Abington, Massachusetts

4.3 mi577 ftgain
ModerateLoop
Cliff Pond Trail
Trail

Cliff Pond Trail

Brewster, Massachusetts

2.7 mi476 ftgain
EasyLoop
Clifford G. Grant Reservation Loop
Trail

Clifford G. Grant Reservation Loop

North Easton, Massachusetts

3.3 mi364 ftgain
ModerateLoop
Clipper City Rail Trail
Trail

Clipper City Rail Trail

Newburyport, Massachusetts

2.2 mi180 ftgain
EasyOut & Back
Cochichewick Loop
Trail

Cochichewick Loop

North Andover, Massachusetts

5.4 mi928 ftgain
ModerateLoop
Coco, Pinecone, Rocky Road, Moore Loop
Trail

Coco, Pinecone, Rocky Road, Moore Loop

Framingham, Massachusetts

2.4 mi262 ftgain
EasyLoop
Codman South Loop
Trail

Codman South Loop

Waverley, Massachusetts

1.0 mi82 ftgain
EasyLoop
Coffee House Loop
Trail

Coffee House Loop

Douglas, Massachusetts

2.4 mi305 ftgain
EasyLoop
Colby Philips Trail via Hanover Greenway
Trail

Colby Philips Trail via Hanover Greenway

Hanover, Massachusetts

3.8 mi607 ftgain
ModerateLoop
Cold Harbor Trail
Trail

Cold Harbor Trail

Northborough, Massachusetts

4.3 mi423 ftgain
ModerateOut & Back
Cold Spring Park
Trail

Cold Spring Park

Waban, Massachusetts

1.5 mi161 ftgain
EasyLoop
Cole Forest Blue, Yellow and White Trail Loop
Trail

Cole Forest Blue, Yellow and White Trail Loop

Southbridge, Massachusetts

1.5 mi381 ftgain
EasyLoop
College Rock Run
Trail

College Rock Run

Hopkinton, Massachusetts

1.8 mi213 ftgain
ModerateOut & Back
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