38 Trails in Dover, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
Diamond Hill State Park Advanced difficulty 10.0 ***** Cumberland
Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
Vietnam Trails Intermediate difficulty 20.0 **** Milford
Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
Horn Pond Intermediate difficulty 13 **** Woburn
F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
Landlocked Forest Intermediate difficulty 7 **** Burlington
Borderland State Park Intermediate difficulty 7.0 **** Sharon
Cutler Park Beginner difficulty 6 **** Newton Highlands
Western Greenway Intermediate difficulty 8.0 **** Belmont
Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
Beaver Brook North Intermediate difficulty 4.0 **** Belmont
Beaver Pond Advanced difficulty 7.0 **** Franklin
Weston College Land Beginner difficulty 5.0 **** Weston
Prospect Hill Beginner difficulty 10.0 **** Waltham
Blue Hills Intermediate difficulty 5.0 **** Milton
Callahan State Park Beginner difficulty 10.0 **** Framingham
Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
Hale Reservation Beginner difficulty 10.0 **** Westwood
Adams Farm Intermediate difficulty 10.0 **** Walpole
Needham Town Forest Intermediate difficulty 7.0 *** Needham
Belmont Conservation Beginner difficulty 10.0 *** Belmont
Ashland State Park Intermediate difficulty 7.0 *** Ashland
Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
Boxborough Area Trails Intermediate difficulty 10.0 *** Boxborough
Caryl Park Beginner difficulty 17.0 *** Dover
Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
Whipple Hill Beginner difficulty 4.0 *** Lexington
Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
Charles River Loop Easiest difficulty 15 ** Boston
Rocky Woods Beginner difficulty 7.0 ** Medfield
Jerico Town Forest Beginner difficulty 5.0 ** Weston
Millenium Park Easiest difficulty 12.0 * West Roxbury
Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
Littles Brook difficulty 2.0 Burlington
Chestnut Hill Reservoir Loop difficulty 2 Boston

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