Few optics are finer than pulling into a quiet New England harbor before a classic-yacht race and beholding myriad gorgeous yachts, their lovely sheer lines and gleaming brightwork set against a backdrop of hardwood trees in full summer trim. The tradition of racing classic yachts remains strong in New England, and recently has been bolstered by the Classic Yacht Owners Association and its Classic Yacht Challenge Series, which this summer drew dozens of iconic participants and delivered great racing on some of the country’s most storied waters. The Classic Yacht Owners Association was founded in 2015, with the aim of bolstering camaraderie among classic-yacht owners. One of the most important ways they’ve accomplished this was by joining existing New England classic-yacht regattas into a greater tri-regional circuit that includes Maine, Massachusetts, Rhode Island, Connecticut and New York. Yacht owners must compete in five races across two of the three regions and be CYOA members to compete for the series’ overall awards. These rules encourage sailors and yachts to travel, meet new friends, and share ideas and classic-yacht culture.
In 2021, this circuit included the August Herreshoff Marine Museum and the America’s Cup Hall of Fame’s Classic Yacht Regatta & Rendezvous, which celebrated its 50th-anniversary Golden Jubilee at its Bristol, Rhode Island, facility. The Jubilee featured three days of racing on Narragansett Bay, après-sail socializing, and a high-spirited dinner. Some of the Jubilee’s 33-strong fleet included the Sparkman & Stephens-designed Dorade (1929), the Herreshoff NY40 Marilee (1926), the Sparkman & Stephens-designed Mah Jong (1957), the Herreshoff R Class Racing Sloop Gamecock (1925), and the 12 Metres Nefertiti, Onawa and Weatherly.
On-the-water competition was energetic, but splinters aren’t popular. “There are some [racecourse] interactions that are closer than anyone would like to see, but for the most part, it’s about enjoying racing these beautiful boats with friends, and then relaxing onshore with an adult beverage or two,” said Bill Lynn, president and executive director of the Herreshoff Marine Museum and the America’s Cup Hall of Fame. “No one wants to see these boats damaged, and no one wants to deal with the aftermath, so people are generally pretty well-behaved.”
The 2021 regatta calendar also included the New York Yacht Club’s June Tiedemann Classics Regatta, which took place off Newport; the July Boothbay Harbor Yacht Club Regatta and Shipyard Cup Classics Challenge off Boothbay Harbor, Maine; and the September 42nd-Annual IYRS Newport Classic Yacht Regatta, which unfurled on the waters of Narragansett Bay and Rhode Island Sound. Three other August events—the Castine Classic Yacht Race, the Camden to Brooklin Feeder Race and the Eggemoggin Reach Regatta—gave crews an opportunity to participate in separate events that collectively served as a three-day affair.
Chris Culver’s classic 12 Meter Onawa took top prize in the Newport Classic’s Vintage Class, while Thorpe Leeson’s Katrina collected first place in the regatta’s Classic Class, and Ted Boynton’s Dagger stitched up honors in the Spirit of Tradition Class.
The season ended with the September Indian Harbor Yacht Club’s Classic Yacht Regatta and the Hempstead Harbour Club’s Heritage Cup Regatta and Rendezvous. A glance at the 2021 Classic Yacht Challenge Series entry reveals the usual suspects traveling the circuit. Which, of course, is exactly what the Classic Yacht Owners Association envisioned when they created this visually stunning series. Classic-yacht lovers and sailors were treated to a full press of sail, and many are already planning on joining the 2022 CYCS events. Just be forewarned: Classic yachts can emit their own (highly romantic) gravitational pull.