46 Trails in Boston, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
World's End Beginner difficulty 5.0 *** Hingham
Wompatuck State Park Intermediate difficulty 15.0 **** Hingham
Whitney And Thayer Woods/weir River Farm Beginner difficulty 10.0 *** Cohasset
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
Swan Pond Road Trails Easiest difficulty 7 ** Middleton
Russell Mill Intermediate difficulty 7.0 **** Chelmsford
Rocky Woods Beginner difficulty 7.0 ** Medfield
Reading Town Forest difficulty 5.0 Reading
Prospect Hill Beginner difficulty 10.0 **** Waltham
Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
Needham Town Forest Intermediate difficulty 7.0 *** Needham
Millenium Park Easiest difficulty 12.0 * West Roxbury
Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
Lynn Woods Reservation Intermediate difficulty 0 **** Saugus
Littles Brook difficulty 2.0 Burlington
Landlocked Forest Intermediate difficulty 7 **** Burlington
Jerico Town Forest Beginner difficulty 5.0 ** Weston
Horn Pond Intermediate difficulty 13 **** Woburn
Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
Harold Parker State Forest Advanced difficulty 35 ***** Andover
Hale Reservation Beginner difficulty 10.0 **** Westwood
Great Esker Park Intermediate difficulty 5.0 ** Weymouth
Great Brook State Park Beginner difficulty 15.0 *** Carlise
F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
Duxbury Intermediate difficulty 8.0 **** Duxbury
Cutler Park Beginner difficulty 6 **** Newton Highlands
Chestnut Hill Reservoir Loop difficulty 2 Boston
Chebacco Woods Intermediate difficulty 10.0 ***** Hamilton
Charles River Loop Easiest difficulty 15 ** Boston
Caryl Park Beginner difficulty 17.0 *** Dover
Carolina Hill Intermediate difficulty 10.0 **** Marshfield
Cannon Hills Intermediate difficulty 1 *** Salem Ma
Borderland State Park Intermediate difficulty 7.0 **** Sharon
Blue Hills Intermediate difficulty 5.0 **** Milton
Billerica State Forest Intermediate difficulty 9 ***** Billerica
Beverly Commons Advanced difficulty 10 **** Beverly
Belmont Conservation Beginner difficulty 10.0 *** Belmont
Beaver Brook North Intermediate difficulty 4.0 **** Belmont
Beals Cove Park Beginner difficulty 5.0 ** Hingham
Ames Nowell Intermediate difficulty 10.0 *** Abington
Adams Farm Intermediate difficulty 10.0 **** Walpole

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