At 18 Main Street in Stockbridge is a house known as the “Sedgwick Little House” or the Erik Erikson House. Its earliest section was originally a large cottage built c. 1855 (other dates claimed for the house are 1850 and the 1870s). In 1896, the property was acquired by Henry Dwight Sedgwick III, prominent Stockbridge resident and one of the well-known Sedgwick family. The Sedgwick Pie in Stockbridge Cemetery is the famous burial place of the Sedgwick family. In 1898, Henry D. Sedgwick built “the Sedgwick Little House” (the central section of the current Colonial Revival mansion) for his son Alexander (1867-1929). This seems to have replaced the original cottage (?). The house was later expanded through additions made between 1898 and 1908. The east and west wings were added by Edward L. Morse, who bought the house in 1908. Later, the house was purchased by the well-known writer and psychoanalyst Erik Erikson, who was working at the Austin Riggs Center at the time. The house is now a bed & breakfast called the Taggart House.

Built circa 1890 and designed by Delano & Aldrich, the Brown Caldwell House is located at 23 Main Street in Stockbridge. In 1930, the house was sold to the Austin Riggs Center. In 1907, while recuperating from tuberculosis in Stockbridge, New York internist Dr. Austen Fox Riggs began to expand his interest in psychiatry and psychology, developing a new and innovative treatment program. He founded The Stockbridge Institute for the Study and Treatment of the Psychoneuroses, which was incorporated in 1919 as the Austen Riggs Foundation. The house was remodeled (its pedimented portico was removed) to become Foundation Inn, one of several historic buildings that comprise the campus of the Austin Riggs Center.