38 Trails in Winchester, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Harold Parker State Forest Advanced difficulty 35 ***** Andover
Lowell-Dracut-Tyngsborough State Forest Advanced difficulty 10.0 **** Lowell
Billerica State Forest Intermediate difficulty 9 ***** Billerica
Lynn Woods Reservation Intermediate difficulty 0 **** Saugus
Needham Town Forest Intermediate difficulty 7.0 *** Needham
Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
Georgetown-rowley State Forest Intermediate difficulty 9.0 **** Georgetown
Great Esker Park Intermediate difficulty 5.0 ** Weymouth
Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
Beaver Brook North Intermediate difficulty 4.0 **** Belmont
Ward Reservation Intermediate difficulty 12.0 ***** Andover
Western Greenway Intermediate difficulty 8.0 **** Belmont
Russell Mill Intermediate difficulty 7.0 **** Chelmsford
Landlocked Forest Intermediate difficulty 7 **** Burlington
Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
Horn Pond Intermediate difficulty 13 **** Woburn
Cutler Park Beginner difficulty 6 **** Newton Highlands
Belmont Conservation Beginner difficulty 10.0 *** Belmont
Willowdale Forest Beginner difficulty 20.0 **** Wenham
Bald Hill Reservation Beginner difficulty 10.0 *** Boxford
Great Brook State Park Beginner difficulty 15.0 *** Carlise
Beals Cove Park Beginner difficulty 5.0 ** Hingham
Merrimack River Trail Beginner difficulty 10.0 **** Andover
Hale Reservation Beginner difficulty 10.0 **** Westwood
Whipple Hill Beginner difficulty 4.0 *** Lexington
Caryl Park Beginner difficulty 17.0 *** Dover
Weston College Land Beginner difficulty 5.0 **** Weston
Prospect Hill Beginner difficulty 10.0 **** Waltham
Bradley Palmer Beginner difficulty 11.0 *** Topsfield
Jerico Town Forest Beginner difficulty 5.0 ** Weston
Charles River Loop Easiest difficulty 15 ** Boston
Swan Pond Road Trails Easiest difficulty 7 ** Middleton
Millenium Park Easiest difficulty 12.0 * West Roxbury
Reading Town Forest difficulty 5.0 Reading
Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
Littles Brook difficulty 2.0 Burlington
Root Ball (Harold Parker State Forest) difficulty 0.29 Andover
Chestnut Hill Reservoir Loop difficulty 2 Boston

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