38 Trails in Winchester, Massachusetts

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

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