The Canadian Power and Sail Squadron was organized in the spring of 1938 in Windsor, Ontario with G. William Bowman as first Commander. The Detroit Power Squadron, formed some 25 years ahead of Windsor, played a considerable part in our early beginnings, both by example and by education. Another partner in our beginnings was the Windsor Yacht Club, which came into existence only shortly before us. The title Canadian Power Squadron was quickly replaced by the title Canadian Power Squadrons as the Sarnia, London and Toronto Squadrons soon were formed. For over 75 years, the Windsor Power and Sail Squadron has been involved locally, regionally and nationally in providing leadership in education and the promotion of the ideas of the Canadian Power and Sail Squadrons.

The pennant of the Windsor Power and Sail Squadron consists of a red circle on the hoist half, which is the international symbol for the number one. The outer half of the pennant consists of the nine blue and white bars of the National Flag. The combination is intended to signify Windsor as the first Canadian Power Squadron. Immediately inside of the hoist is a vertical platinum diamond bar, signifying the Windsor squadron having attained its 75th year in existence.