Elected Supervisors of the Town of Southold

• 1860-1864 John Ireland
• 1864-1872 Franklyn H. Overton
• 1873 Stuart G. Terry
• 1874-1880 Henry A. Reeves
• 1881-1882 Franklyn H. Overton
• 1883-1893 Henry A. Reeves
• 1894-1906 Barton D. Skinner
• 1907-1910 G. Frank Tuthill
• 1911-1912 Llewellyn F. Terry
• 1913-1914 Henry A. Reeve
• 1915-1926 David W. Tuthill
• 1927-1928 John Hoffman
• 1929-1930 Charles T. Brooks
• 1931-1932 John Hoffman
• 1933-1946 S. Wentworth Horton
• 1947-1959 Norman E. Klipp
• 1960 Henry Tuthill (elected Supervisor, killed in December 1960 auto accident, Lester M. Albertson appointed Supervisor)
• 1969 Lester M. Albertson (elected Suffolk County Clerk, Albert M. Martocchia appointed Supervisor)
• 1969-1979 Albert M. Martocchia (died June 26, 1979; July 24, 1979 James Homan appointed Supervisor)
• 1980-1983 William R. Pell III
• 1984-1989 Francis J. Murphy
• 1990-1993 Scott L. Harris
• 1994-1995 Thomas H. Wickham
• 1996-2001 Jean W. Cochran
• 2002-2005 Joshua Y. Horton
• 2006 - Scott A. Russell

First Elected Women Officials in Southold Town

• Edna Ankers Brown served as Southold Town assessor from 1960 until 1972
• First woman Town Clerk in Southold Town: Judith T. Terry, sworn in as Town Clerk on January 1976 and served until December 1997
• First woman Supervisor of Southold Town: Jean Cochran. She also served on the Town Board as Councilwoman