In the early 1780s, Leonard Proctor and Salmon Dutton and their families, moved from Massachusetts and settled in present-day Cavendish, Vermont and gave their names to the two major settlements on the Black River, Proctorsville and Duttonsville. Leonard Proctor was born in Westford, Massachusetts and fought in the Revolutionary War at a young age. He settled in Cavendish in 1782 and built a modest house/tavern, and underwent developing the village in his name, Proctorsville. By the early 1800s, Leonard was a highly esteemed member of town and had the funds to erect the finest Federal style manse in the village, to showcase the stability and wealth of his community. The home exhibits scalloped cornice moldings and the carved wood flowering vines springing from urns on the upper pilasters that have a folk/Federal quality that stands out as a very unique design detail. Carved Adamesque bell flowers that flank the door suggest Asher Benjamin’s Windsor influence. Elliptical sunbursts above the pilasters, elaborate guilloche friezes, and the broad semielliptical attic light have a later Federal character. It is possible that Leonard had this house built, and it was “modernized” by one of his heirs.