The History of the Opera House Cup
The Beginning - 1973
Over several summer evenings in 1973, a small group of sailors gathered at the Opera House Restaurant on South Water Street — a Nantucket institution owned by the charismatic Gwen Gaillard.
Among the regulars were young sailors, liveaboards, and wooden boat enthusiasts who shared a love of classic yachts and spirited storytelling. On one late July night, the idea was born: why not stage a wooden boat race in Gwen’s honor?
“How 'bout we have a wooden boat race?”
With raised glasses and unanimous enthusiasm, the germ of an idea became reality. That August, the first Opera House Cup was sailed on Nantucket Sound. Gwen Gaillard, along with restaurant manager Charles “Chick” Walsh and local sailors including Dick Deutsch and Tony Topping, helped organize the inaugural race — drawing up courses, starts, and rules with the skippers themselves.
What began as a spontaneous celebration of wooden boats and camaraderie soon became a Nantucket tradition.
Growth & Recognition
In the decades that followed, the Opera House Cup evolved from a local wooden boat race into a premier classic yacht regatta.
Today, the event attracts some of the most distinguished classic yachts in the world. It is part of the CYOA Classic Yacht Series and scored under the CRF rating system.
The beloved Rainbow Parade at Brant Point, the Parade of Wooden Boats, and the Awards Party at Jetties Beach have become defining traditions of Nantucket Race Week.
A Nantucket Tradition
Now in its fifth decade, the Opera House Cup remains a celebration of craftsmanship, seamanship, and island hospitality — honoring the legacy of its founders while welcoming a new generation of sailors each summer.
