45 Trails in Natick, 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
West Hill Dam Intermediate difficulty 5.0 **** Upton
Vietnam Trails Intermediate difficulty 20.0 **** Milford
Upton State Forest Beginner difficulty 12.0 *** Upton
Rocky Woods Beginner difficulty 7.0 ** Medfield
Rattlesnake Hill Advanced difficulty 7.0 ***** Bolton
Prospect Hill Beginner difficulty 10.0 **** Waltham
Peppercorn Hill Intermediate difficulty 3.0 *** Upton
Oak Hill Advanced difficulty 8.0 **** Littleton
Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
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
Mendon Town Forest Intermediate difficulty 7.0 **** Mendon
Littles Brook difficulty 2.0 Burlington
Landlocked Forest Intermediate difficulty 7 **** Burlington
Lake Whitehall Advanced difficulty 7.0 *** Hopkinton
Jerico Town Forest Beginner difficulty 5.0 ** Weston
Horn Pond Intermediate difficulty 13 **** Woburn
Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
Hale Reservation Beginner difficulty 10.0 **** Westwood
Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
Fort Rock difficulty 7.0 Littleton
F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
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
Callahan State Park Beginner difficulty 10.0 **** Framingham
Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
Boxborough Area Trails Intermediate difficulty 10.0 *** Boxborough
Borderland State Park Intermediate difficulty 7.0 **** Sharon
Blue Hills Intermediate difficulty 5.0 **** Milton
Belmont Conservation Beginner difficulty 10.0 *** Belmont
Beaver Pond Advanced difficulty 7.0 **** Franklin
Beaver Brook North Intermediate difficulty 4.0 **** Belmont
Ashland State Park Intermediate difficulty 7.0 *** Ashland
Adams Farm Intermediate difficulty 10.0 **** Walpole

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