43 Trails in Hopkinton, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Douglas State Forest Intermediate difficulty 27.0 **** Douglas
Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
Vietnam Trails Intermediate difficulty 20.0 **** Milford
Grafton Land Trust Intermediate difficulty 20.0 *** Grafton
Caryl Park Beginner difficulty 17.0 *** Dover
Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
Plummer's Landing/ Goat Hill Advanced difficulty 15.0 **** Whitinsville
Singletary Trails Intermediate difficulty 15.0 **** Millbury
Upton State Forest Beginner difficulty 12.0 *** Upton
Sutton State Forest Intermediate difficulty 12.0 **** Sutton
Black Hut Management Area difficulty 11.0 Glendale
F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
Rayburn Trails Intermediate difficulty 10.0 **** Millbury
Prospect Hill Beginner difficulty 10.0 **** Waltham
Hale Reservation Beginner difficulty 10.0 **** Westwood
Adams Farm Intermediate difficulty 10.0 **** Walpole
Callahan State Park Beginner difficulty 10.0 **** Framingham
Diamond Hill State Park Advanced difficulty 10.0 ***** Cumberland
Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
Mt. Pisgah Intermediate difficulty 8.0 **** Northborough
Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
Mendon Town Forest Intermediate difficulty 7.0 **** Mendon
Rattlesnake Hill Advanced difficulty 7.0 ***** Bolton
Ashland State Park Intermediate difficulty 7.0 *** Ashland
Lake Whitehall Advanced difficulty 7.0 *** Hopkinton
Beaver Pond Advanced difficulty 7.0 **** Franklin
Rocky Woods Beginner difficulty 7.0 ** Medfield
Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
West Hill Dam Intermediate difficulty 5.0 **** Upton
Jerico Town Forest Beginner difficulty 5.0 ** Weston
Green Hill Park Advanced difficulty 5.0 **** Worcester
Yellow Beginner difficulty 5.0 *** Worcester
Weston College Land Beginner difficulty 5.0 **** Weston
Colt Farm difficulty 5.0 North Smithfield
Cold Harbor Brook Intermediate difficulty 5.0 *** Northborough
Vaughn Hill/bower Spring Trail System(s) Advanced difficulty 4.0 **** Bolton/harvard
Libby Trail difficulty 4.0 Westborough
Peppercorn Hill Intermediate difficulty 3.0 *** Upton
Middle School Loop Beginner difficulty 3.0 *** Nasonville
Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick

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