40 Trails in Weston, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Oak Hill Advanced difficulty 8.0 **** Littleton
Harold Parker State Forest Advanced difficulty 35 ***** Andover
Billerica State Forest Intermediate difficulty 9 ***** Billerica
Needham Town Forest Intermediate difficulty 7.0 *** Needham
Vietnam Trails Intermediate difficulty 20.0 **** Milford
Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
Boxborough Area Trails Intermediate difficulty 10.0 *** Boxborough
Western Greenway Intermediate difficulty 8.0 **** Belmont
Beaver Brook North Intermediate difficulty 4.0 **** Belmont
Russell Mill Intermediate difficulty 7.0 **** Chelmsford
Landlocked Forest Intermediate difficulty 7 **** Burlington
Ashland State Park Intermediate difficulty 7.0 *** Ashland
Blue Hills Intermediate difficulty 5.0 **** Milton
Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
Horn Pond Intermediate difficulty 13 **** Woburn
Adams Farm Intermediate difficulty 10.0 **** Walpole
Cutler Park Beginner difficulty 6 **** Newton Highlands
Belmont Conservation Beginner difficulty 10.0 *** Belmont
Callahan State Park Beginner difficulty 10.0 **** Framingham
Great Brook State Park Beginner difficulty 15.0 *** Carlise
Whipple Hill Beginner difficulty 4.0 *** Lexington
Hale Reservation Beginner difficulty 10.0 **** Westwood
Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
Weston College Land Beginner difficulty 5.0 **** Weston
Prospect Hill Beginner difficulty 10.0 **** Waltham
Caryl Park Beginner difficulty 17.0 *** Dover
Rocky Woods Beginner difficulty 7.0 ** Medfield
Jerico Town Forest Beginner difficulty 5.0 ** Weston
Charles River Loop Easiest difficulty 15 ** Boston
Millenium Park Easiest difficulty 12.0 * West Roxbury
Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
Reading Town Forest difficulty 5.0 Reading
Littles Brook difficulty 2.0 Burlington
Fort Rock difficulty 7.0 Littleton
Special Ops (♦) difficulty 0.68 Groton
Chestnut Hill Reservoir Loop difficulty 2 Boston

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