Distance 40 miles
Williamstown — North Adams — Mount Greylock
Begin and end in Williamstown, home of Williams College, one of the nation’s best undergraduate schools and certainly one of the prettiest on a fall day. Round out your cultural quotient at the Sterling & Francine Clark Art Institute (“The Clark”), known for its outstanding collection of French impressionists, Old Masters and American artists. The Chef’s Hat restaurant, also in Williamstown, serves lunch, but it’s better for breakfast if you’re craving turnip muffins.
The highlight of this route is the Mount Greylock Scenic Byway, whose hairpin turns will bring you to the highest point in Massachusetts, from which you can see five states and every gradation of fall color. Each Columbus Day, hundreds of hikers do the Mount Greylock Ramble, a tough climb to the 3,491-foot summit—which is why most people drive it.
Route: From Williamstown, Rte. 2 E 5 mi. At Rte. 8 S, turn right almost immediately onto Mt. Greylock Scenic Byway: follow it 18 mi. Rte. 7 N 17 mi. to Williamstown. Alternatively, Rte. 7 S 11 mi. to Lenox.