Hiking Trails in Massachusetts
Discover 1,642 routes with difficulty, elevation, and trail stats. Built for quickly narrowing down the right hike.
Winnekenni Shoreline Loop
Haverhill, Massachusetts
4.2 mi696 ftgain
TrailModerateLoop
Winniekinnie Castle Trail
Haverhill, Massachusetts
2.7 mi413 ftgain
TrailModerateLoop
Winterberry Way, Harrys Way, and Otter Alley Loop
Maynard, Massachusetts
2.7 mi322 ftgain
TrailEasyLoop
Winterberry Way, Taylor Way and Harry's Way Loop
Sudbury, Massachusetts
4.8 mi551 ftgain
TrailModerateLoop
Winthrop Hill and Bear Hill Loop
Stoneham, Massachusetts
1.9 mi223 ftgain
TrailModerateLoop
Witch Hollow Loop
Boxford, Massachusetts
2.3 mi112 ftgain
TrailEasyLoop
Witches' Cove and Plymton Trail
Marlborough, Massachusetts
2.3 mi187 ftgain
TrailEasyLoop
Witches' Cove, Plymton, Desert Loop, Cranberrt Brook, Ocean By-Pass Loop
Marlborough, Massachusetts
5.2 mi436 ftgain
TrailModerateLoop
Wolcott Hill Loop Trail
Milton, Massachusetts
2.3 mi522 ftgain
TrailModerateLoop
Wolcott Path and Puddle Path to Hemenway Hill
Milton, Massachusetts
2.9 mi568 ftgain
TrailModerateOut & Back
Wolcott Path to Eliot Tower
Milton, Massachusetts
2.2 mi538 ftgain
TrailModerateOut & Back
Wolf Meadow Road to High Rock to Dan's Trail Loop
Foxborough, Massachusetts
4.4 mi702 ftgain
TrailModerateLoop
Wolf Meadow Trail
Foxborough, Massachusetts
2.1 mi367 ftgain
TrailEasyOut & Back
Wolf Rock Trail to Crow Hill to Redemption Rock to Wachusett Pop
Westminster, Massachusetts
9.1 mi2,313 ftgain
TrailDifficultLoop
Wollomonopoag Conservation Area Loop
Wrentham, Massachusetts
2.3 mi331 ftgain
TrailEasyLoop
Wompatuck South Loop
Norwell, Massachusetts
8.7 mi1,152 ftgain
TrailDifficultLoop
Wompatuck State Park Big Loop
Hingham, Massachusetts
10.3 mi1,371 ftgain
TrailDifficultLoop
Woodland and Boulder Loops
South Dartmouth, Massachusetts
1.6 mi174 ftgain
TrailEasyLoop
Woodland Nature Loop
Stow, Massachusetts
1.0 mi98 ftgain
TrailEasyLoop
Woodland Wonderland Trail
Edgartown, Massachusetts
2.5 mi210 ftgain
TrailEasyLoop
Woodsom Farm North
Amesbury, Massachusetts
3.1 mi482 ftgain
TrailModerateOut & Back
Woolsey and Aspinwall Loop
Lenox, Massachusetts
1.7 mi302 ftgain
TrailEasyLoop
Woolsey, Lookout, Coakley, Weaver, Aspinwall Loop
Lenox, Massachusetts
2.6 mi479 ftgain
TrailEasyLoop
Worcester East Side and Blue Trail
Worcester, Massachusetts
6.7 mi1,286 ftgain
TrailModerateOut & Back