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.

The first Mayor’s Cup Race, June 1, 1986, was heavily promoted in local media from Westchester County to New Haven. The Race drew nearly 100 entries and in quickly established itself as an annual event on the yachting calendar, the first major regatta of every boating season on Western Long Island Sound. The Race is officially sanctioned by the Yacht Racing Association of Long Island Sound, and is a qualifying race for five YRA-LIS annual awards: the Gitana, Sappho, Rudder, Kings Point, and Mertz trophies.

Typically, the Mayor’s Cup Race is organized into competitive divisions for both spinnaker-equipped and non-spinnaker yachts, handicapped appropriately. They race on various courses and over various distances (usually 7-15 nautical miles depending upon prevailing weather conditions). The yachts race around buoys in local waters within an area ranging from Greenwich and Norwalk on the North shore of Long Island Sound, to Oyster Bay and Huntington Harbor on the South shore of the Sound. The annual Mayor’s Cup Race is typically  held on the 2nd Sunday in June and the Race is always followed by a reception and colorful awards ceremony for captains and their racing crews on the grounds of the Halloween Yacht Club. The reception following the Race is said by many to be more fun than the Race itself.  The Mayor of Stamford generally attends and assists with the trophy presentations.

For several years the Mayor’s Cup Race offered only trophies to the fastest boats in each division and a "Mayor’s Cup" -- a large silver champagne bucket -- to the fastest yacht among the several division winners. In 1993, expanding the trophy list, The Halloween Yacht Club trophy was also offered. Whereas the Mayor’s Cup is presented to the captain of the fastest boat among the several winners in spinnaker divisions, The Halloween Yacht Club trophy is now presented to the captain of the fastest boat among the several non-spinnaker divisions. Other trophies for competitors who finish first, second, or third within their respective divisions are also awarded.

The trophy presentations were expanded again in 1999, when the City of Stamford Cup was added; this trophy is awarded annually to the guest club whose yachts earn, as a group, the best results in the Mayor’s Cup Race. (The best four finishers from a guest club overall win the trophy for that club.) Please refer to other pages on this web site for descriptions of past winners of these trophies. Permanent plaques listing all the winners of past Mayor’s Cup trophies are kept at our Clubhouse and in the trophy case at Stamford City Hall.

The Mayor’s Cup Race is organized and managed by a committee of volunteer HYC members. As it has grown, managing the Race has become a year-round function. All the trophies, supplies, and other materials for the Race are purchased out of modest entry fees provided by those who participate in the Race. There is no cost to our Club’s treasury. Similarly, there is no cost to the Club for the reception following the Race. The Race’s expenses are also offset, in part, by local organizations which contribute to the race. One of our biggest and most consistent supporters has been Landfall Navigation, a local retail merchant.

Since 1996, receipts in excess of expenses have been donated to a local charitable organization. Most recently that has been the Young Mariners program of the Stamford Sailing Foundation, a 501(c)3 non-profit that offers at-risk public school children sailing instruction and other opportunities to enjoy Long Island Sound.

New for 2004, the RC welcomed the local cat boat fleet. The cats, ranging in length from 18-24 feet, were started in their own level division, raced for their own trophies, and fought among themselves.