221 Trails in Massachusetts

Trail Name Difficulty Length (mi) Rating City
Yellow Beginner difficulty 5.0 *** Worcester
Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
World's End Beginner difficulty 5.0 *** Hingham
Wompatuck State Park Intermediate difficulty 15.0 **** Hingham
Wolftree trail, Bittersweet,Dragon tail, Dave's Pass, Moonwort difficulty 6.0 Adams
Wma Trail Beginner difficulty 3.0 ***** Wilbraham
Willowdale Forest Beginner difficulty 20.0 **** Wenham
Willow Street Trails Intermediate difficulty 15.0 **** Yarmouth
Wilbraham/Hampden Loop Intermediate difficulty 6.0 * Springfield
Whitney And Thayer Woods/weir River Farm Beginner difficulty 10.0 *** Cohasset
Whites Reservior difficulty 16.0 Westhampton
Whipple Hill Beginner difficulty 4.0 *** Lexington
Weston College Land Beginner difficulty 5.0 **** Weston
Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
Western Greenway Intermediate difficulty 8.0 **** Belmont
West Hill Dam Intermediate difficulty 5.0 **** Upton
West Barnstable Conservation Area Intermediate difficulty 12.0 **** West Barnstable
Wendell State Forest Intermediate difficulty 17.0 ***** Wendell
Wells State Park Intermediate difficulty 10.0 **** Sturbridge
Wellfleet Ponds Beginner difficulty 20.0 **** Wellfleet
Weir hill Easiest difficulty 5.0 ** North Andover
Waskosims Rock difficulty 5.0 **** West Tisbury
Ware River Rail trail difficulty 7.0 *** Barre
Ward Reservation Intermediate difficulty 12.0 ***** Andover
Volunteer Park/Chatham Ponds Beginner difficulty 7.0 * Chatham
Village Park/ Abrams Rock Intermediate difficulty 5.0 ***** Swansea
Vietnam Trails Intermediate difficulty 20.0 **** Milford
Vaughn Hill/bower Spring Trail System(s) Advanced difficulty 4.0 **** Bolton/harvard
Upton State Forest Beginner difficulty 12.0 *** Upton
Unknown difficulty 3.0 Hadley
Tully Lake Advanced difficulty 0.0 **** Royalston
Townsend State Forest Beginner difficulty 15.0 *** Townsend
Tisbury Meadow difficulty 7.0 Vineyard Haven
Thunder Mountain Bike Park (Berkshire East) Advanced difficulty 5.0 ***** Charlemont
The Groton Wildlife Sanctury/Lawrence Woods difficulty 10.0 Groton
The Boulders Beginner difficulty 6.0 *** Dalton
Tantasqua jr high difficulty 15.0 Fiskdale
Talbot Trails Advanced difficulty 8.0 ** Northboro
Swan Pond Road Trails Easiest difficulty 7 ** Middleton
Sutton Water Works Intermediate difficulty 5.0 **** Sutton
Sutton State Forest Intermediate difficulty 12.0 **** Sutton
Sugarloaf Mt/Pucumtuck trail difficulty 5.0 South Deerfield
Springside park difficulty 4.0 Pittsfield
Special Ops (♦) difficulty 0.68 Groton
South Groton Trails difficulty 10.0 Groton
Singletary Trails Intermediate difficulty 15.0 **** Millbury
Sheep Pond Woodland Hills Conservation difficulty 3.0 Brewster
Shawme-Crowell State Forest difficulty 10.0 Sandwich
Sha-nah-nah difficulty 0.0 Wilbraham
Sawmill Hills Conservation Area Intermediate difficulty 8.0 **** Northampton

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