Conversations with Classic Boats

Conversations with Classic Boats is a podcast about classic boat designs and the stories behind them. Hosted by Tom Darling, this episode chronicles the Golden Jubilee of the granddaddy of East Coast classic regattas – the Opera House Cup in Nantucket Sound north of the 46 square mile island known for its whaling history and grey shingled architecture.

In 1972, the race was the result of a bar bet with two local restaurateurs, Gwen Gaillard and her partner Chick Walsh, proprietors of the watering hole by Nantucket Harbor. Nine boats competed back then; tradition is the winner receives the coveted carved and gilded quarterboard carrying the winning boats name.

Fifty years later, five dozen wooden boats, both antique and newly built Spirit of Tradition models, will be sailing a triangular course on August 21 of between 20 to 25 miles. Only the 2022 Eggomogin Reach race in Maine, counting 112 entries this year, will have a bigger classics roster.

The new feature of the last several years of COVID has been the use of the pursuit start format. Smallest boats first, bigger boats chase. First boat to the finish wins.

The first grouping will be over a dozen Nantucket Alerions, the 26 foot locally built versions of Captain N. G. Herreshoff’s own personal knockabout, Alerion III, now in the Mystic Seaport Museum small boat collection. Alerions have won multiple Opera House Cups as recently as 2019.

The big boats in the fleet include 12 Meters like Weatherly, the Rhodes-designed winner of the 1962 America’s Cup, the W Class Wild Horses and the 1932 creation of L.F. Herreshoff, Big Ti aka Ticonderoga. A separate class for schooners includes Brilliant, Olin Stephens venerable schooner dating to 1932.

Another long-time feature of Opera House Cup weekend is the Classic Yacht Exhibition. Twenty-three classics, including the work of 13 great designers, will be available for viewing by the public the day before the race. This exhibition attracts visitors from yachts people to Nantucket locals as a benefit for Nantucket Community Sailing.

The morning of the race also features the Rainbow Parade, a procession of the local Beetle Cat fleet sporting their colored sails. The Opera House Cup fleet will line up for their own Parade of Wooden Boats on its way out the channel to the starting line.