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.

Recently, our docks have had a wonderful makeover, having all new wood replaced on the much needed older runs.

The Halloween Yacht  Club was founded in 1926 by Commodore Al Phillips and 16 other fishermen with small boats. They acquired several acres of waterfront property by leasing it from the City. This lease is renewed periodically, and today, although the Club owns its clubhouse, the Club still leases the property from the City of Stamford. It is the only parkland that generates revenue for the City of Stamford.

The leased property was, and still is, part of a larger municipal park. This land, on the shores of Long Island Sound, was originally owned by the Homer S. Cummings Family, which willed the land to the City of Stamford. The City took title to Cummings property on Halloween Eve, 1926, and thus the original name, Halloween Park.

The name of the Park was subsequently changed back to “Cummings” to honor the family and its gift, but that portion of the land dedicated to the yacht club retained the Halloween name. The founding Commodore of the Club was Alfred N. Phillips, Jr. Commodore Phillips was a popular man about town. He had been Mayor of Stamford and Representative to the United States Congress. One of the Club members, a local commercial artist, designed the Club’s first burgee to include a black witch riding her black broom on an orange field — Halloween colors. And so the name Halloween Yacht Club was established and remains to this day.