Cheshire has 3 hiking trails. These trails range from 0.6 to 7.6 miles in length. The most popular trail is Cheshire Cobbles and Gore Pond. Trails.com member JARED O. recently completed Cheshire Cobbles and Gore Pond.
Cheshire Cobbles and Gore PondView Trail Details
A fantastic vista point and the solitude of a scenic pond are the major rewards of this out-and-back hike along the Appalachian Trail.
Mount Greylock State Reservation-Jones Nose and Rounds RockView Trail Details
A delightful ramble along Greylock’s midslopes features stunning
vistas, prolific blueberry barrens, and a small plane crash site from
Old Adams RoadView Trail Details
Old Adams Road is a hiking trail in Cheshire, Massachusetts. It is 0.6 miles long and begins at 2,360 feet altitude. Traveling the entire trail ...