37 Trails in Winchester, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Harold Parker State Forest Advanced 35.0 ***** Andover
Weston Aquaduct and Unused Rail Loop 25.0 Weston
Willowdale Forest Beginner 20.0 **** Wenham
Caryl Park Beginner 17.0 *** Dover
Charles River Loop Easiest 15.0 ** Boston
Great Brook State Park Beginner 15.0 *** Carlise
Horn Pond Intermediate 13.0 **** Woburn
Millenium Park Easiest 12.0 * West Roxbury
Ward Reservation Intermediate 12.0 ***** Andover
Bradley Palmer Beginner 11.0 *** Topsfield
Hale Reservation Beginner 10.0 **** Westwood
Bald Hill Reservation Beginner 10.0 *** Boxford
Prospect Hill Beginner 10.0 **** Waltham
Merrimack River Trail Beginner 10.0 **** Andover
Belmont Conservation Beginner 10.0 *** Belmont
Lowell-Dracut-Tyngsborough State Forest Advanced 10.0 **** Lowell
Georgetown-rowley State Forest Intermediate 9.0 **** Georgetown
Billerica State Forest Intermediate 9.0 ***** Billerica
Middlesex Fells Reservation Intermediate 8.0 **** Winchester
Mill Pond Conservation Area Intermediate 8.0 **** Burlington
Western Greenway Intermediate 8.0 **** Belmont
Landlocked Forest Intermediate 7.0 **** Burlington
Needham Town Forest Intermediate 7.0 *** Needham
Russell Mill Intermediate 7.0 **** Chelmsford
Swan Pond Road Trails Easiest 7 ** Middleton
Cutler Park Beginner 6.0 **** Newton Highlands
Weston College Land Beginner 5.0 **** Weston
Jerico Town Forest Beginner 5.0 ** Weston
Reading Town Forest 5.0 Reading
Beals Cove Park Beginner 5.0 ** Hingham
Great Esker Park Intermediate 5.0 ** Weymouth
Beaver Brook North Intermediate 4.0 **** Belmont
Whipple Hill Beginner 4.0 *** Lexington
Littles Brook 2.0 Burlington
Henry S. Hunnewell Town Forest Intermediate 1.0 ***** Natick
Root Ball (Harold Parker State Forest) 0.29 Andover
Lynn Woods Reservation Intermediate 0 ****