221 Trails in Massachusetts

Trail Name Difficulty Length (mi) Rating City
Pine Meadow Conservation Area difficulty 5.0 Ayer
Gregg Woods difficulty 5.0 Dunstable
Village Park/ Abrams Rock Intermediate difficulty 5.0 ***** Swansea
Brooks Woodland Preserve difficulty 5.0 Petersham
Weston College Land Beginner difficulty 5.0 **** Weston
Mass Autobahn Beginner difficulty 5.0 ** Attleboro Ma
Religious Trails Beginner difficulty 5.0 *** In Attleboro
West Hill Dam Intermediate difficulty 5.0 **** Upton
Beals Cove Park Beginner difficulty 5.0 ** Hingham
Great Esker Park Intermediate difficulty 5.0 ** Weymouth
World's End Beginner difficulty 5.0 *** Hingham
Fox Run Intermediate difficulty 5.0 *** No. Oxford
Blue Hills Intermediate difficulty 5.0 **** Milton
Springside park difficulty 4.0 Pittsfield
Hampshire College difficulty 4.0 Amherst
Race Leading difficulty 4.0 Amherst
Libby Trail difficulty 4.0 Westborough
Beaver Brook North Intermediate difficulty 4.0 **** Belmont
Whipple Hill Beginner difficulty 4.0 *** Lexington
Vaughn Hill/bower Spring Trail System(s) Advanced difficulty 4.0 **** Bolton/harvard
Nonotuck Park Intermediate difficulty 4.0 *** Easthampton
Freetown State Forest (Bent Rim Trail) Intermediate difficulty 4.0 *** Freetown
Maudslay State Park Intermediate difficulty 4.0 *** Newburyport
Brake Hill (West Newbury / Groveland) difficulty 4 Groveland
Ripleys Field difficulty 3.0 **** Vineyard Haven
Chatham Marshlands Beginner difficulty 3.0 **** Chatham
Covered Bridge difficulty 3.0 Barre
Unknown difficulty 3.0 Hadley
Peppercorn Hill Intermediate difficulty 3.0 *** Upton
John Hyslip difficulty 3.0 Andover
Red Zone (Charlemont trails) Advanced difficulty 3.0 ***** Charlemont
Franklin Dirt jumps Intermediate difficulty 3.0 *** Franklin
Provin Mountain difficulty 3.0 Feeding Hills
Boynton Park Intermediate difficulty 3.0 *** Worcester
Wma Trail Beginner difficulty 3.0 ***** Wilbraham
Howe State Park Beginner difficulty 3.0 ** Spencer
Sheep Pond Woodland Hills Conservation difficulty 3.0 Brewster
Savoy Mountain difficulty 3.0 Savoy Mtn State Park (North Adams)
Purple Trail difficulty 2.0 ***** Edgartown
Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
Boy Scout Trails difficulty 2.0 Franklin
Old Rifle Range difficulty 2.0 Concord, Ma
Newton Hill Easiest difficulty 2.0 ** Worcester
Mount Warner Reservation Beginner difficulty 2.0 *** North Hadley
Dracut conservation trail difficulty 2.0 Dracut
Johns Woods difficulty 2.0 Haverhill
E-stranged Moose Intermediate difficulty 2.0 **** Charlemont
Noon hill difficulty 2.0 Medfield
Beech Saint Conservation Land difficulty 2.0 Rockland
Fork Factory Brook Beginner difficulty 2.0 ** Medfield

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