Directions: Follow Route 7 North from Sheffield to Williamstown. Route 8 runs from Sandisfield to Dalton and between two state forests so you'll get plenty of leaf peeping in early on in the trip. Get on Route 183 and follow the Housatonic River from Great Barrington to Lenox. Take Richmond Road, off Route 183, just south of Tanglewood, and stop at the overlook for views of Stockbridge Bowl and the southern Berkshire Hills. Route 43 East, off Route 7, is the lower road to Williamstown.
Round trip distance: ~ 40 miles
When to go: Late October
Drive provided by MassVacation.com.