Hiking Trails in Massachusetts

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

Wachusett Mountain via Harrington Trail

Wachusett Mountain via Harrington Trail

Princeton, Massachusetts

4.8 km263 mgain
ModerateOut & Back
Wachusett Mountain via North Road and Semuhenna Trails

Wachusett Mountain via North Road and Semuhenna Trails

Westminster, Massachusetts

5.5 km263 mgain
EasyLoop
Wachusett Mountain via Old Indian and Loop Trails

Wachusett Mountain via Old Indian and Loop Trails

Princeton, Massachusetts

3.9 km238 mgain
ModerateLoop
Wachusett Mountain West Side Trail

Wachusett Mountain West Side Trail

Westminster, Massachusetts

4.3 km261 mgain
ModerateLoop
Wachusett Reservoir and French Hill Loop

Wachusett Reservoir and French Hill Loop

West Boylston, Massachusetts

6.0 km188 mgain
ModerateLoop
Wachusett Reservoir and Reservation Trail

Wachusett Reservoir and Reservation Trail

Boylston, Massachusetts

2.3 km79 mgain
ModerateLoop
Wachusett Reservoir Gate 25 Trail

Wachusett Reservoir Gate 25 Trail

West Boylston, Massachusetts

4.7 km172 mgain
EasyLoop
Wachusett Reservoir Hike

Wachusett Reservoir Hike

Clinton, Massachusetts

4.5 km229 mgain
EasyOut & Back
Walden Pond Path

Walden Pond Path

Concord, Massachusetts

2.7 km83 mgain
EasyLoop
Walker Mountain Loop

Walker Mountain Loop

Sturbridge, Massachusetts

4.5 km244 mgain
ModerateLoop
Waseeka Trail

Waseeka Trail

Holliston, Massachusetts

2.9 km71 mgain
EasyLoop
Washington Marsh Loop

Washington Marsh Loop

Medford, Massachusetts

1.8 km34 mgain
EasyLoop
Waskosim's Rock Reservation (Chilmark)

Waskosim's Rock Reservation (Chilmark)

Chilmark, Massachusetts

4.0 km114 mgain
ModerateLoop
Watatic Mountain via Watatic Mountain Road

Watatic Mountain via Watatic Mountain Road

Ashby, Massachusetts

5.2 km231 mgain
ModerateOut & Back
Wayside Forest Loop

Wayside Forest Loop

Sudbury, Massachusetts

1.4 km49 mgain
EasyLoop
Webb Memorial State Park Loop

Webb Memorial State Park Loop

North Weymouth, Massachusetts

2.3 km28 mgain
EasyLoop
Weetamoo Cliff

Weetamoo Cliff

Lynn, Massachusetts

4.7 km110 mgain
ModerateLoop
Weir Hill Reservation Trail

Weir Hill Reservation Trail

North Andover, Massachusetts

4.2 km164 mgain
EasyLoop
Wellesley College to Lake Waban to Fuller Brook Path

Wellesley College to Lake Waban to Fuller Brook Path

Wellesley, Massachusetts

10.1 km259 mgain
ModerateLoop
Wellesley Crosstown Trail

Wellesley Crosstown Trail

Wellesley Hills, Massachusetts

1.8 km28 mgain
EasyPoint to Point
Wells State Park North and South Trail (Red and White)

Wells State Park North and South Trail (Red and White)

Sturbridge, Massachusetts

6.1 km235 mgain
ModerateLoop
Wells State Park North Trail (Red)

Wells State Park North Trail (Red)

Sturbridge, Massachusetts

3.9 km159 mgain
ModerateLoop
Wenakeening Woods and Idylbrook Loop

Wenakeening Woods and Idylbrook Loop

Holliston, Massachusetts

6.6 km128 mgain
EasyLoop
West Barnstable Conservation Area MTB Loop from Crooked Cartway

West Barnstable Conservation Area MTB Loop from Crooked Cartway

Marstons Mills, Massachusetts

14.8 km262 mgain
ModerateLoop