45 Trails in Natick, Massachusetts

Trail Name Difficulty Length (mi) Rating City
Henry S. Hunnewell Town Forest Intermediate 1.0 ***** Natick
Chestnut Hill Reservoir Loop 2 Boston
Boy Scout Trails Intermediate 2.0 *** Franklin
Littles Brook 2.0 Burlington
Peppercorn Hill Intermediate 3.0 *** Upton
Beaver Brook North Intermediate 4.0 **** Belmont
Whipple Hill Beginner 4.0 *** Lexington
Blue Hills Intermediate 5.0 **** Milton
Jerico Town Forest Beginner 5.0 ** Weston
West Hill Dam Intermediate 5.0 **** Upton
Weston College Land Beginner 5.0 **** Weston
Cutler Park Beginner 6 **** Newton Highlands
Gardner Hill Town Forest Intermediate 6.0 *** Stow
Rocky Woods Beginner 7.0 ** Medfield
Lake Whitehall Advanced 7.0 *** Hopkinton
Mendon Town Forest Intermediate 7.0 **** Mendon
Beaver Pond Advanced 7.0 **** Franklin
Landlocked Forest Intermediate 7 **** Burlington
Needham Town Forest Intermediate 7.0 *** Needham
Borderland State Park Intermediate 7.0 **** Sharon
Ashland State Park Intermediate 7.0 *** Ashland
Franklin State Forest Intermediate 7.0 **** Franklin State Forest
Rattlesnake Hill Advanced 7.0 ***** Bolton
Fort Rock 7.0 Littleton
Western Greenway Intermediate 8.0 **** Belmont
Middlesex Fells Reservation Intermediate 8.0 **** Winchester
Noon Hill Reservation Beginner 8.0 *** Medfield
Oak Hill Advanced 8.0 **** Littleton
Adams Farm Intermediate 10.0 **** Walpole
Callahan State Park Beginner 10.0 **** Framingham
Belmont Conservation Beginner 10.0 *** Belmont
Boxborough Area Trails Intermediate 10.0 *** Boxborough
Hale Reservation Beginner 10.0 **** Westwood
Prospect Hill Beginner 10.0 **** Waltham
Hopkinton State Park Intermediate 10.0 **** Hopkinton
Mill Pond Conservation Area Intermediate 10 **** Burlington
F. Gilbert Hills State Park Intermediate 11.0 **** Foxboro
Upton State Forest Beginner 12.0 *** Upton
Millenium Park Easiest 12.0 * West Roxbury
Horn Pond Intermediate 13 **** Woburn
Nobscot Mtn. Intermediate 15.0 *** Sudbury
Charles River Loop Easiest 15 ** Boston
Caryl Park Beginner 17.0 *** Dover
Vietnam Trails Intermediate 20.0 **** Milford
Weston Aquaduct and Unused Rail Loop 25.0 Weston