When the Herreshoff Marine Museum in Bristol, Rhode Island, was first established, I was a rough-around-the-edges teenager. Raised in Montauk, New York, I had no appreciation for fine sailing vessels or what made them go. Yet I followed my passion for boats to an old yard in Three Mile Harbor where an enigmatic little fin-keeled sloop called Jilt intrigued me. A yard worker mumbled “Herreshoff,” which was an altogether new word to me. I took a photo of Jilt and sent it to the Herreshoff Marine Museum, which had recently opened. Halsey C. Herreshoff replied with a handwritten letter saying that I had an eye for fast boats. Jilt was designed by the inventor of the fin-keel, his grandfather Nathanael G. Herreshoff, in 1899. That letter, and the museum, kindled my lifelong appreciation for classic yachts and their history.
I’ve since made multiple pilgrimages to the museum, where I’ve learned about the Herreshoff Manufacturing Company (1878-1945) and how its founders—John B. and Nathanael G. Herreshoff—melded art and engineering to create many of the finest American yachts ever produced. The Hall of Boats holds more than 60 significant designs, and the Model Room has an iconic collection of 500 models.
Over the years, each museum visit has inspired me, so I eagerly attended the Herreshoff Classic Yacht Regatta in August. The event, part of the museum’s golden jubilee celebration, was open to all classics. Herreshoff yachts raced with those by other great designers such as Crowninshield, Sparkman & Stephens, Rhodes, Luders, Mylne and Nathanael Herreshoff’s son, L. Francis Herreshoff. Every winning America’s Cup yacht from 1893 to 1934 was built by Herreshoff, so it’s fitting that four 12-Meters participated in the event: Weatherly, Columbia, Nefertiti and the 1928 Starling Burgess Onawa.
The oldest Herreshoff yachts racing were the 53-foot 1907 daysailer Neith and the 1914 Buzzard’s Bay 25 Bagatelle. Other notable boats included the 1926 NY 40 Marilee, striking in her combination of power and beauty. Three L. Francis Herreshoff boats raced: the schooner Narwal, the Stuart Knockabout Blackwing and the Rozinante ketch Tern owned by myself and my partner Steve Lubitz of Wooden Boatworks in New York.
My favorite participant was the venerable 91-year-old Sparkman & Stephens Dorade, designed with a very narrow beam, balanced ends and a tall Marconi rig—features that shocked the yachting world in 1930. If the definition of “classic” means being judged over time to be outstanding and of the highest quality, Dorade is certainly it. After two restorations the boat’s dedicated owners set a goal to repeat all the major ocean races she won in the 1930s: the Transatlantic, Newport-Bermuda, Fastnet and Transpacific. Dorade matched or bettered her times in all of them. She won the 2013 Transpac 77 years after her first victory, and she finished a full day faster. Classic, indeed.
I learned so much from the Herreshoff yachts I’ve sailed on in the years since my first naive encounter with Halsey Herreshoff. Halsey and I talked boats again during the jubilee weekend as he guided me to his office in the remarkable Burnside Street loft. Photos of famous yachts and historic sailors occupy every square inch of wall space. We chatted about the joys of European sailing and the heightened regard they have for yachting history and classic yacht preservation. I related what an honor it was to be flying the sole American ensign in the classic regattas in Spain while sailing Dolphin, a 1914 Newport 29. He seemed excited when I said I loved showing off Nathanael Herreshoff’s design prowess.
We also discussed the benefits of sailing the right boat at each period of our lives. I just gave up a stalwart 57-foot cruising boat in favor of a more personal small ketch designed by L. Francis Herreshoff. Halsey’s now sailing a performance Alerion 26, his latest design based on his grandfather’s hull form. After giving me a tour of his workshop on the opposite end of the loft, we stopped to look over a large pond sailor Capt. Nat had made. Halsey brightened when I mentioned the magnificently machined brass steering gear looked like the workings of a fine timepiece. “Everything my grandfather made was like that,” he said. Halsey spoke of his grandfather with both nostalgic enthusiasm and technical awe.
Even at 88, Halsey is awesome and ardent. He is ex-president of the museum, but he’s still carrying the Herreshoff torch. With a naval architecture and marine engineering degree from the Webb Institute and his master’s from M.I.T., he’s been a lifelong designer of custom and production yachts and he’s still at it. He founded the America’s Cup Hall of Fame on site and he’s been bowman, tactician and navigator on 12-Meters, with four successful Americas Cup defenses. About racing Halsey said, “The essential thing is the crew.”
So when he invited me to race with him, I was completely flattered. However, my partner, Steve, and I had brought our own Herreshoff up to the race. I had a Sophie’s choice moment: I could elect to sail with Halsey on his Alerion or sail on my own Rozinante. With apologies to my partner, I chose to sail with Halsey and his design assistant Nick Barron, 22, himself a Webb Institute man, who Halsey wryly noted is “exactly one fourth my age.”
On race day, we boarded Halsey’s 75-year-old launch Bubble, his grandfather’s WWII design. With vintage can-do looks and chain-and-sprocket steering, the 21-foot launch was living history. While aboard Bubble, we came alongside Halsey’s newest creation, Dazzler, based on Capt. Nat’s 1914 “improved” Alerion Sadie. Halsey’s version lacks a stern deck and cabin, transforming her into an open boat. With the same handsome looks of an Alerion, but more developed, she’s updated with swept spreaders and winches abreast the mast. All halyards and foredeck lines are efficiently controlled from an array of clutches mounted aft of the breakwater. One can reach everything with ease in the unrestricted cockpit, much appreciated for spinnaker work. The boat’s jib furling system is a combination headstay roller-furler and sliding outhaul on a jib boom, which articulates vertically when furled. “My father’s design,” Halsey noted. That’s A. Sidney DeWolf Herreshoff, the other naval architect in the family.
During the regatta, five classes sailed two triangular courses, starting with 12 knots of northeast breeze, building sharply as the afternoon progressed. The best part of a classic regatta is observing the yachts as they deserve to be seen: underway. The big boats put on an awesome display of power and grace while the 12-Meters executed precise tacking duels. We scrutinized performance and trim on the competition. Because we were in the same starting group, my own boat Tern seemed stuck to Dazzler like Velcro, and I found my heart in two different cockpits. I mentioned how stiff Tern looked in the building breeze and Halsey—a man of few words while on board—sternly said, “I’m not going to talk about any other boat except the one we’re sailing.” But he did notice she was keeping up and eventually asked dryly, “Is that double-ender your boat?” Enough said.
We tacked up the beach on the east side of the course as the breeze built. Through rocky patches and behind seawalls, we took shelter from the foul current pouring out under Bristol’s Mount Hope Bridge. Many sailors stayed in deeper water in the teeth of the current and quickly lost ground. A combination of Halsey’s moxie and a handheld GPS allowed us to hide inshore from the opposing current.
The strategy worked, but it was wet going in a steep, shallow chop, with lots of short tacking. With the bottom rising up and the beach looming a few yards ahead, Halsey certainly tested our nerves as we held on to advantage. We exhaled after each tack away from the shore. Halsey grumbled as he pushed the tiller over, “I guess we shouldn’t get selfish and hang on too long.”
This article was originally published in the November 2021 issue.
