From Boston to coastal towns and former mill cities, these historic spots reveal the side of Massachusetts that never made it onto the classroom chalkboard. The African School operated here, giving children access to education at a time when that was a radical act. The Ashley House at 117 Cooper Hill Road in Sheffield, Massachusetts, is the oldest standing house in Berkshire County, built in 1735. There is a Shaker Museum, the first of its kind in the United States, alongside a Native American Museum and an Art Museum. When Historic New England founder William Sumner Appleton acquired the property in 1919, it was in serious disrepair.