Hiking Trails in Massachusetts
Discover 1,218 routes with difficulty, elevation, and trail stats. Built for quickly narrowing down the right hike.
Trail
Whitehall Reservoir Loop
Hopkinton, Massachusetts
7.0 mi1,283 ftgain
ModerateLoop
Trail
Whitetail Woods Loop
Littleton, Massachusetts
0.8 mi85 ftgain
EasyLoop
Trail
Whiting Street Reservoir Loop
Holyoke, Massachusetts
3.8 mi715 ftgain
ModerateLoop
Trail
Whitney and Thayer Woods Trail
Cohasset, Massachusetts
3.7 mi479 ftgain
ModerateLoop
Trail
Wild Acres Park
Pittsfield, Massachusetts
1.2 mi200 ftgain
EasyLoop
Trail
Wildcat Hill via Red Diamond to Bay Circuit Loop
Ashland, Massachusetts
3.1 mi476 ftgain
ModerateLoop
Trail
Willard Brook and Friends Loop
Ashby, Massachusetts
3.2 mi505 ftgain
ModerateLoop
Trail
Willard Brook Trail
Ashby, Massachusetts
2.2 mi246 ftgain
EasyOut & Back
Trail
Willard Woods
Lexington, Massachusetts
2.7 mi305 ftgain
EasyLoop
Trail
Williams Trail
Williamstown, Massachusetts
3.0 mi1,266 ftgain
ModerateLoop
Trail
Willow Spring Path and North Dam Road
Winchester, Massachusetts
2.3 mi289 ftgain
ModerateLoop
Trail
Wills Hole Conservation Land and Nara Park Loop
Acton, Massachusetts
2.5 mi256 ftgain
EasyLoop
Trail
Wilson Mountain Reservation Trail
Dedham, Massachusetts
1.6 mi220 ftgain
EasyLoop
Trail
Winchendon Rail Trail
Winchendon, Massachusetts
1.7 mi246 ftgain
EasyOut & Back
Trail
Windsor Dam
Belchertown, Massachusetts
1.6 mi292 ftgain
EasyLoop
Trail
Winnekenni Shoreline Loop
Haverhill, Massachusetts
4.2 mi696 ftgain
ModerateLoop
Trail
Winterberry Way, Harrys Way, and Otter Alley Loop
Maynard, Massachusetts
2.7 mi322 ftgain
EasyLoop
Trail
Winterberry Way, Taylor Way and Harry's Way Loop
Sudbury, Massachusetts
4.8 mi551 ftgain
ModerateLoop
Trail
Winthrop Hill and Bear Hill Loop
Stoneham, Massachusetts
1.9 mi223 ftgain
ModerateLoop
Trail
Witches' Cove and Plymton Trail
Marlborough, Massachusetts
2.3 mi187 ftgain
EasyLoop
Trail
Witches' Cove, Plymton, Desert Loop, Cranberrt Brook, Ocean By-Pass Loop
Marlborough, Massachusetts
5.2 mi436 ftgain
ModerateLoop
Trail
Wolcott Hill Loop Trail
Milton, Massachusetts
2.3 mi522 ftgain
ModerateLoop
Trail
Wolcott Path and Puddle Path to Hemenway Hill
Milton, Massachusetts
2.9 mi568 ftgain
ModerateOut & Back
Trail
Wolcott Path to Eliot Tower
Milton, Massachusetts
2.2 mi538 ftgain
ModerateOut & Back