The Opera House Cup was born one hot, summer night in July 1973; the place was the Opera House Restaurant, a fine-dining and drinks club on Nantucket Island. Owner Gwen Gaillard and manager Chick Walsh were sitting at a table on the patio watching the diners finish up as the Ship's Inn crew and other locals began to trickle in. The drinks flowed and discussion eventually came around to the sailors' main complaint; no one held a regatta for classic single-hulled wooden sailboats. "I'll provide the food, drinks, and winner's cup," Gwen said. "You guys go out and get the boats." That night the Opera House Cup Regatta was born.

For the last 33 years on the third Sunday of every August, the world's most beautifully crafted and designed sailboats have gathered in the Nantucket harbor. The Opera House Cup has become a summer spectator tradition as the rainbow fleet escorts the boats past Brant Point lighthouse to the starting point.