31 Trails in Milton, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Wrentham State Forest Advanced 17.0 ***** Wrentham
Wompatuck State Park Intermediate 15.0 **** Hingham
Lynn Woods Reservation Intermediate 0 ****
Middlesex Fells Reservation Intermediate 8.0 **** Winchester
F. Gilbert Hills State Park Intermediate 11.0 **** Foxboro
Landlocked Forest Intermediate 7.0 **** Burlington
Borderland State Park Intermediate 7.0 **** Sharon
Cutler Park Beginner 6.0 **** Newton Highlands
Weston College Land Beginner 5.0 **** Weston
Beaver Brook North Intermediate 4.0 **** Belmont
Prospect Hill Beginner 10.0 **** Waltham
Horn Pond Intermediate 13.0 **** Woburn
Western Greenway Intermediate 8.0 **** Belmont
Blue Hills Intermediate 5.0 **** Milton
Hale Reservation Beginner 10.0 **** Westwood
Adams Farm Intermediate 10.0 **** Walpole
Needham Town Forest Intermediate 7.0 *** Needham
Belmont Conservation Beginner 10.0 *** Belmont
Ames Nowell Intermediate 10.0 *** Abington
Noon Hill Reservation Beginner 8.0 *** Medfield
Caryl Park Beginner 17.0 *** Dover
Whitney And Thayer Woods/weir River Farm Beginner 10.0 *** Cohasset
World's End Beginner 5.0 *** Hingham
Whipple Hill Beginner 4.0 *** Lexington
Charles River Loop Easiest 15.0 ** Boston
Rocky Woods Beginner 7.0 ** Medfield
Jerico Town Forest Beginner 5.0 ** Weston
Beals Cove Park Beginner 5.0 ** Hingham
Great Esker Park Intermediate 5.0 ** Weymouth
Millenium Park Easiest 12.0 * West Roxbury
Weston Aquaduct and Unused Rail Loop 25.0 Weston