Hiking Trails in Massachusetts

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

Whipple Hill Reserve

Whipple Hill Reserve

Lexington, Massachusetts

3.4 km89 mgain
EasyLoop
Whistling Cave and Nuthatch Loop

Whistling Cave and Nuthatch Loop

Upton, Massachusetts

6.6 km223 mgain
ModerateLoop
White Dot and Red Dot Loop Trail

White Dot and Red Dot Loop Trail

Jefferson, Massachusetts

4.8 km178 mgain
EasyLoop
White Hall Road and Park Road Loop

White Hall Road and Park Road Loop

Upton, Massachusetts

6.1 km160 mgain
ModerateLoop
White Triangle Trail

White Triangle Trail

Milton, Massachusetts

9.7 km277 mgain
ModerateLoop
Whitehall Reservoir Loop

Whitehall Reservoir Loop

Hopkinton, Massachusetts

11.3 km391 mgain
ModerateLoop
Whitetail Woods Loop

Whitetail Woods Loop

Littleton, Massachusetts

1.3 km26 mgain
EasyLoop
Whiting Street Reservoir Loop

Whiting Street Reservoir Loop

Holyoke, Massachusetts

6.1 km218 mgain
EasyLoop
Whitney and Thayer Woods Trail

Whitney and Thayer Woods Trail

Cohasset, Massachusetts

6.0 km146 mgain
EasyLoop
Wild Acres Park

Wild Acres Park

Pittsfield, Massachusetts

1.9 km61 mgain
EasyLoop
Wildcat Hill via Red Diamond to Bay Circuit Loop

Wildcat Hill via Red Diamond to Bay Circuit Loop

Ashland, Massachusetts

5.0 km145 mgain
EasyLoop
Willard Brook and Friends Loop

Willard Brook and Friends Loop

Ashby, Massachusetts

5.2 km154 mgain
ModerateLoop
Willard Brook Trail

Willard Brook Trail

Ashby, Massachusetts

3.5 km75 mgain
EasyOut & Back
Willard Woods

Willard Woods

Lexington, Massachusetts

4.3 km93 mgain
EasyLoop
Williams Trail

Williams Trail

Williamstown, Massachusetts

4.8 km386 mgain
EasyLoop
Willow Spring Path and North Dam Road

Willow Spring Path and North Dam Road

Winchester, Massachusetts

3.7 km88 mgain
ModerateLoop
Wills Hole Conservation Land and Nara Park Loop

Wills Hole Conservation Land and Nara Park Loop

Acton, Massachusetts

4.0 km78 mgain
EasyLoop
Wilson Mountain Reservation Trail

Wilson Mountain Reservation Trail

Dedham, Massachusetts

2.6 km67 mgain
EasyLoop
Winchendon Rail Trail

Winchendon Rail Trail

Winchendon, Massachusetts

2.7 km75 mgain
EasyOut & Back
Windsor Dam

Windsor Dam

Belchertown, Massachusetts

2.6 km89 mgain
EasyLoop
Winnekenni Shoreline Loop

Winnekenni Shoreline Loop

Haverhill, Massachusetts

6.8 km212 mgain
EasyLoop
Winterberry Way, Harrys Way, and Otter Alley Loop

Winterberry Way, Harrys Way, and Otter Alley Loop

Maynard, Massachusetts

4.3 km98 mgain
EasyLoop
Winterberry Way, Taylor Way and Harry's Way Loop

Winterberry Way, Taylor Way and Harry's Way Loop

Sudbury, Massachusetts

7.7 km168 mgain
EasyLoop
Winthrop Hill and Bear Hill Loop

Winthrop Hill and Bear Hill Loop

Stoneham, Massachusetts

3.1 km68 mgain
ModerateLoop
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