32 Trails in Milton, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
Borderland State Park Intermediate difficulty 7.0 **** Sharon
Lynn Woods Reservation Intermediate difficulty 0 **** Saugus
Needham Town Forest Intermediate difficulty 7.0 *** Needham
F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
Western Greenway Intermediate difficulty 8.0 **** Belmont
Wompatuck State Park Intermediate difficulty 15.0 **** Hingham
Beaver Brook North Intermediate difficulty 4.0 **** Belmont
Great Esker Park Intermediate difficulty 5.0 ** Weymouth
Landlocked Forest Intermediate difficulty 7 **** Burlington
Ames Nowell Intermediate difficulty 10.0 *** Abington
Blue Hills Intermediate difficulty 5.0 **** Milton
Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
Horn Pond Intermediate difficulty 13 **** Woburn
Adams Farm Intermediate difficulty 10.0 **** Walpole
Cutler Park Beginner difficulty 6 **** Newton Highlands
Belmont Conservation Beginner difficulty 10.0 *** Belmont
Beals Cove Park Beginner difficulty 5.0 ** Hingham
Caryl Park Beginner difficulty 17.0 *** Dover
World's End Beginner difficulty 5.0 *** Hingham
Prospect Hill Beginner difficulty 10.0 **** Waltham
Hale Reservation Beginner difficulty 10.0 **** Westwood
Weston College Land Beginner difficulty 5.0 **** Weston
Whitney And Thayer Woods/weir River Farm Beginner difficulty 10.0 *** Cohasset
Whipple Hill Beginner difficulty 4.0 *** Lexington
Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
Rocky Woods Beginner difficulty 7.0 ** Medfield
Jerico Town Forest Beginner difficulty 5.0 ** Weston
Charles River Loop Easiest difficulty 15 ** Boston
Millenium Park Easiest difficulty 12.0 * West Roxbury
Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
Chestnut Hill Reservoir Loop difficulty 2 Boston

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