The Halloween Yacht Club was founded in 1926 by Commodore Alfred N. Phillips, Jr. and 16 other fishermen with small boats. They acquired several acres of waterfront property and a boathouse by leasing an unused portion of Cummings Park (then known as Halloween Park) from the City of Stamford. Subject to periodic renewals, that lease is still in effect today.
Phillips was the Club’s founding Commodore. He was an accomplished sailor who served three different terms as Mayor of Stamford, and was later elected to 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 came into being and remains to this day.
Additional interesting details of the history of the Club can be found in the book by Stamford resident Ronald Marcus – “What’s in the name …” (Stamford History Center).
A bit of trivia: The Halloween Yacht Club burgee is one of only three yacht club flags that displays a witch. The other clubs are the Salem (Massachusetts) Yacht Club (the witch is an obvious symbol for this historic club’s flag), and the Greenwich (Connecticut) Boat & Yacht Club. The witch on the Greenwich club’s burgee is green (“Green Witch,” got it?).