Principal Port Washington September 1882

In 1882, Stephen's daughter, Leoria, is 1 1/2 years old and he is residing in Binghamton. Two hundred miles away the principal of Port Washington school, Mr. H. W. Allen, receives an appointment in the New York Custom House. He starts immediately which leaves the position of principal at the Port Washington School vacant and Stephen takes over as principal.

Ten years prior, S. D. Wilbur served as the principal of the nearby Southold, Long Island school for a short time before becoming a School Commissioner of Broome County for nine years.