41 Trails in Weston, Massachusetts

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

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