Even before its founding in 1641, the City of Stamford has been a sea-faring town. It was a major port of entry for merchandise shipped here from the United Kingdom, Netherlands, and elsewhere in Europe; it was a dispatch point for agricultural and manufactured products being distributed by sea to New York City, other colonies and to Europe; and it was a major fishing community as well. Some of the earliest community leaders in Stamford were merchants who initially established their reputations as sea captains during the early 1600s, Captains Turner and Underhill among them. Acknowledging this rich maritime history, today the seal of the City of Stamford features a three-masted schooner at its crest.
In 1986, The Mayor’s Cup Race was initiated
— according to an official proclamation issued by then-Mayor Thom Serrani — to maintain Stamford’s association with the sea, and to “… foster community spirit and expand our community’s pride in one of our City’s greatest natural resources, our waterfront, while highlighting one of our favorite recreational activities, boating.” Also, the Race — hosted by a true community yacht club, Halloween — fosters splendid community spirit and extraordinary community pride.” Bernie Weiss, who was Commodore in 1986, at that time reminded HYC members that “… the City is our landlord, and our lease with the City obligates us to serve Stamford’s public interests. The Mayor’s Cup Race is both a glorious and a painless way for us to do that.” Since Day 1, The Mayor’s Cup Race has been co-sponsored by Halloween Yacht Club and the City of Stamford.