Mount Greylock via AT

Mount Greylock at 3491 feet is the highest point in Massachusetts and one of the finest summit destinations along the Appalachian Trail in New England. The AT ascends from the south via the Cheshire Cobbles trailhead in the town of Cheshire, climbing through northern hardwood forest and then spruce-fir forest characteristic of the higher Berkshires elevations, a 7.6-mile out-and-back with substantial but steady climbing.

The summit hosts the Bascom Lodge, a fieldstone and timber lodge built by the CCC in the 1930s that provides meals and overnight accommodations managed by the Appalachian Mountain Club. Rising directly above the lodge is the 93-foot Veterans War Memorial Tower, a granite lighthouse-style monument dedicated to Massachusetts war veterans, visible from 70 miles on clear days and a beloved Berkshires landmark since 1932.

Views from the summit and tower encompass five states on clear days: Massachusetts, Vermont, New Hampshire, New York, and Connecticut. The Hopper, a glacially carved bowl on the western slope, is visible from the summit area and is one of the finest examples of a cirque in southern New England. The AT continues north from the summit toward Vermont. A road also accesses the summit, so the top can be crowded regardless of trail traffic. Water is available at the lodge. Herman Melville wrote Moby-Dick while viewing Greylock from his Pittsfield home.