32 Trails in Upton, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Diamond Hill State Park Advanced difficulty 10.0 ***** Cumberland
Vietnam Trails Intermediate difficulty 20.0 **** Milford
Plummer's Landing/ Goat Hill Advanced difficulty 15.0 **** Whitinsville
Rayburn Trails Intermediate difficulty 10.0 **** Millbury
Singletary Trails Intermediate difficulty 15.0 **** Millbury
Sutton State Forest Intermediate difficulty 12.0 **** Sutton
Mendon Town Forest Intermediate difficulty 7.0 **** Mendon
Green Hill Park Advanced difficulty 5.0 **** Worcester
Beaver Pond Advanced difficulty 7.0 **** Franklin
Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
Douglas State Forest Intermediate difficulty 27.0 **** Douglas
Callahan State Park Beginner difficulty 10.0 **** Framingham
Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
Mt. Pisgah Intermediate difficulty 8.0 **** Northborough
West Hill Dam Intermediate difficulty 5.0 **** Upton
Walkabout Trail/george Washington Management Area Intermediate difficulty 8.0 *** Chepachet
Grafton Land Trust Intermediate difficulty 20.0 *** Grafton
Ashland State Park Intermediate difficulty 7.0 *** Ashland
Upton State Forest Beginner difficulty 12.0 *** Upton
Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
Peppercorn Hill Intermediate difficulty 3.0 *** Upton
Cold Harbor Brook Intermediate difficulty 5.0 *** Northborough
Middle School Loop Beginner difficulty 3.0 *** Nasonville
Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
Yellow Beginner difficulty 5.0 *** Worcester
Lake Whitehall Advanced difficulty 7.0 *** Hopkinton
Newton Hill Easiest difficulty 2.0 ** Worcester
Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
Colt Farm difficulty 5.0 North Smithfield
Black Hut Management Area difficulty 11.0 Glendale
Libby Trail difficulty 4.0 Westborough

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