Hiking Trails in Massachusetts
Discover 1,642 routes with difficulty, elevation, and trail stats. Built for quickly narrowing down the right hike.
Oakland Trailwalk
Wilbraham, Massachusetts
1.1 mi112 ftgain
TrailEasyLoop
October Farm Loop
Concord, Massachusetts
3.3 mi535 ftgain
TrailModerateLoop
October Mountain Loop
Lee, Massachusetts
7.0 mi1,703 ftgain
TrailDifficultLoop
Old Colony Rail Trail
Harwich, Massachusetts
6.6 mi587 ftgain
TrailModeratePoint to Point
Old Eastern Marsh Trail
Salisbury, Massachusetts
3.0 mi240 ftgain
TrailModerateOut & Back
Old Farm Trail
Marlborough, Massachusetts
2.1 mi407 ftgain
TrailModerateOut & Back
Old Harbor Yellow, Blue, Green, and Red Loop
Westport, Massachusetts
1.9 mi364 ftgain
TrailEasyLoop
Old King Trail
Truro, Massachusetts
3.8 mi217 ftgain
TrailEasyOut & Back
Old Lighthouse Road Trail
Vineyard Haven, Massachusetts
1.7 mi89 ftgain
TrailEasyLoop
Old Manchester-Essex, Pulpit, Ancient Line and Cedar Swamp Trail Loop
Manchester, Massachusetts
4.5 mi276 ftgain
TrailEasyLoop
Old North Bridge Walk
Concord, Massachusetts
2.2 mi259 ftgain
TrailEasyOut & Back
Old Pasture Loop
Wareham, Massachusetts
1.5 mi138 ftgain
TrailEasyLoop
Old Prospect Road to Ward Trail Loop
Andover, Massachusetts
2.8 mi387 ftgain
TrailModerateLoop
Old Purgatory Loop Trail
Sutton, Massachusetts
0.8 mi115 ftgain
TrailEasyLoop
Old Quissett to Stonewall to Inman Hill to East Loop
Mendon, Massachusetts
2.0 mi259 ftgain
TrailModerateLoop
Old Summit Road Trail
Sharon, Massachusetts
1.7 mi184 ftgain
TrailEasyLoop
Olivia's Overlook Via Charcoal Trail
Richmond, Massachusetts
2.0 mi650 ftgain
TrailModerateLoop
Oogamak, Ravine and Nedobak Loop
Florence, Massachusetts
2.4 mi417 ftgain
TrailEasyLoop
Opacum Woods Loop
Sturbridge, Massachusetts
3.0 mi430 ftgain
TrailEasyLoop
Orange and Blue Loop around Old Reservoir
Bedford, Massachusetts
1.4 mi226 ftgain
TrailModerateLoop
Orange and Yellow Loop
North Billerica, Massachusetts
2.2 mi348 ftgain
TrailEasyLoop
Orange Loop Trail
Bedford, Massachusetts
0.9 mi89 ftgain
TrailEasyLoop
Osgood Hill Loop via Osgood Hill Trail to Summit Trail
North Andover, Massachusetts
2.3 mi463 ftgain
TrailModerateLoop
Osprey Marsh
Marion, Massachusetts
0.7 mi69 ftgain
TrailEasyOut & Back