32 Trails in Milton, Massachusetts

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

Know of a new mountain bike trail not listed here? Please tell us about it using this form. Find mountain bike trails near you or for even more trail inspiration and how we ranked the mountain bike trails, see this list of the best mountain bike trails in the world.