Designed by Ian C. MacCallum in 1967, the flag was adopted by the Commissioners of the Town of St. Michaels as the official flag of St. Michaels, Maryland in 1970. The copyright is held by the St. Michaels Museum at St. Mary’s Square.
The flag was originally designed in strict accord with the rules and language of heraldry as the seal of the St. Mary’s Square Museum. It refers to Saint Michaels-on-the-Waters with its sword of the Archangel Michael in the colors of Maryland with a background of white waves on water, referring to the narrow spit of land that St. Michaels sits on between the Miles River and San Domingo Creek. It is colored blue to recall the sailors’ wish for “fair wind and blue water.”