45 Trails in Boston, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Adams Farm Intermediate 10.0 **** Walpole
Ames Nowell Intermediate 10.0 *** Abington
Beals Cove Park Beginner 5.0 ** Hingham
Beaver Brook North Intermediate 4.0 **** Belmont
Belmont Conservation Beginner 10.0 *** Belmont
Beverly Commons Advanced 10 **** Beverly
Billerica State Forest Intermediate 9 ***** Billerica
Blue Hills Intermediate 5.0 **** Milton
Borderland State Park Intermediate 7.0 **** Sharon
Cannon Hills Intermediate 1 *** Salem Ma
Carolina Hill Intermediate 10.0 **** Marshfield
Caryl Park Beginner 17.0 *** Dover
Charles River Loop Easiest 15 ** Boston
Chebacco Woods Intermediate 10.0 ***** Hamilton
Cutler Park Beginner 6 **** Newton Highlands
Duxbury Intermediate 8.0 **** Duxbury
F. Gilbert Hills State Park Intermediate 11.0 **** Foxboro
Great Brook State Park Beginner 15.0 *** Carlise
Great Esker Park Intermediate 5.0 ** Weymouth
Hale Reservation Beginner 10.0 **** Westwood
Harold Parker State Forest Advanced 35 ***** Andover
Henry S. Hunnewell Town Forest Intermediate 1.0 ***** Natick
Horn Pond Intermediate 13 **** Woburn
Jerico Town Forest Beginner 5.0 ** Weston
Landlocked Forest Intermediate 7 **** Burlington
Littles Brook 2.0 Burlington
Lynn Woods Reservation Intermediate 0 ****
Middlesex Fells Reservation Intermediate 8.0 **** Winchester
Mill Pond Conservation Area Intermediate 10 **** Burlington
Millenium Park Easiest 12.0 * West Roxbury
Needham Town Forest Intermediate 7.0 *** Needham
Noon Hill Reservation Beginner 8.0 *** Medfield
Prospect Hill Beginner 10.0 **** Waltham
Reading Town Forest 5.0 Reading
Rocky Woods Beginner 7.0 ** Medfield
Russell Mill Intermediate 7.0 **** Chelmsford
Swan Pond Road Trails Easiest 7 ** Middleton
Western Greenway Intermediate 8.0 **** Belmont
Weston Aquaduct and Unused Rail Loop 25.0 Weston
Weston College Land Beginner 5.0 **** Weston
Whipple Hill Beginner 4.0 *** Lexington
Whitney And Thayer Woods/weir River Farm Beginner 10.0 *** Cohasset
Wompatuck State Park Intermediate 15.0 **** Hingham
World's End Beginner 5.0 *** Hingham
Wrentham State Forest Advanced 17.0 ***** Wrentham