Rockwell Road, Mount Greylock, Massachusetts
Sitting at 3,491 feet, Mount Greylock is the tallest mountain in the Old Bay State. The 10-mile ascent on Rockwell Road, built by the Civilian Conservation Corps in the late 1930’s, is the more gradual way up and traverses through switchbacks and tight curves to the Memorial Tower at the summit, which serves up a 90 mile view on a clear day.