28 Trails in Newton Highlands, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Whipple Hill Beginner difficulty 4.0 *** Lexington
Weston College Land Beginner difficulty 5.0 **** Weston
Weston Aquaduct and Unused Rail Loop  difficulty 25.0 Weston
Western Greenway Intermediate difficulty 8.0 **** Belmont
Rocky Woods Beginner difficulty 7.0 ** Medfield
Prospect Hill Beginner difficulty 10.0 **** Waltham
Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
Needham Town Forest Intermediate difficulty 7.0 *** Needham
Millenium Park Easiest difficulty 12.0 * West Roxbury
Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
Lynn Woods Reservation Intermediate difficulty 0 **** Saugus
Littles Brook  difficulty 2.0 Burlington
Landlocked Forest Intermediate difficulty 7 **** Burlington
Jerico Town Forest Beginner difficulty 5.0 ** Weston
Horn Pond Intermediate difficulty 13 **** Woburn
Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
Hale Reservation Beginner difficulty 10.0 **** Westwood
Cutler Park Beginner difficulty 6 **** Newton Highlands
Chestnut Hill Reservoir Loop  difficulty 2 Boston
Charles River Loop Easiest difficulty 15 ** Boston
Caryl Park Beginner difficulty 17.0 *** Dover
Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
Blue Hills Intermediate difficulty 5.0 **** Milton
Belmont Conservation Beginner difficulty 10.0 *** Belmont
Beaver Brook North Intermediate difficulty 4.0 **** Belmont
Ames Nowell Intermediate difficulty 10.0 *** Abington
Adams Farm Intermediate difficulty 10.0 **** Walpole

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