40 Trails in Weston, Massachusetts

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

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