By Tom Darling

Dolphin in action. The Newport 29’s 29-foot waterline is even longer when the boat is heeled. © Yana Copek/

Two classic Herreshoff designs, conceived Thanksgiving 1913 and born July 4, 1914. On August 18, 2019, they met on a racecourse for the first time in their sailing histories. This is the story of “The Herreshoff Twins,” a pair of Newport 29s named Dolphin and Mischief, and of their younger distant cousin, Rogue.

The Twins are two of four Newport 29s, 35’ 6” overall, over eight tons displacement, and clouds of sail for inshore racers their size. The third boat, named Paddy, was later renamed Teaser and owned by George Byers at Northport Yacht Club in Long Island. The fourth and last built, Comet, was lost in the Hurricane of 1938 in Stonington, CT.

Two vintage Herreshoff boats (pronounced “Hera-sof,” say veteran boat historians), identical twins, never on the same water in a race, came together in competition for the first time in their 105-year lives. The venue was the 47th Opera House Cup in Nantucket, the second event of the Classic Yacht Owners Association’s 2019 Classic Yachts Challenge Series. Their stories are a study in 20th century yacht racing and preservation of the rich heritage of the modern wooden boat era.

The Newport 29, as you see in the accompanying pictures of Dolphin and Mischief, was quite unlike the large, gaff-rigged speedsters such as the New York 50 launched just a few years before. Those older designs were a derivation of Captain Nathanael Herreshoff’s behemoth America’s Cup defenders like Reliance in 1903, the largest AC boat ever built. These boats were long in the overhang, wet, with very tall rigs serviced by professional crews, and not without danger.

Dolphin and Mischief were boats designed for an amateur owner. They were originally gaff- or gunter-rigged, a rig preferred by Herreshoff for shorthanded sailing. Their graceful concave bow sections reflected Capt. Nat’s trip to Bermuda, where he saw the Bermuda fitted dinghy in Hamilton Harbor. The new design, the Newport 29, was conceived for a production run of four boats, and intended for shorthanded daysailing and racing.

The Twins had identical specifications ordered by the two mothers of two teenage sons in the fall of 1913. Mischief was purchased by Mrs. E .B Auchincloss of Newport. Oliver G. Jennings of Connecticut bought Dolphin. The price fully fitted was $3,900. During their construction, both boats had to coexist in the same Burnside Avenue production line in Bristol with the America’s Cup defender of their time, Resolute, a metal monster six times their size. But when they were finished, they went in opposite directions, Dolphin west to Stonington, Mischief south to the Chesapeake. We were bound to reunite them in August 2019.

The Newport 29: Radical departure in fast cruiser design philosophy

The original Newport 29 design, 35 feet, 6 inches long, was a complete departure from the last of the grand topsail gaff rigs of boats like the New York 50 Spartan, winner of her class in the 2019 Opera House Cup. Instead of continuing the relatively short waterlines and massive sail plan designs of the NY 40s and 50s, the Newport 29 was thoroughly modern for a design before World War I.

Born with gaff rigs, both boats took on Marconi rigs in the 1920s. The other new Herreshoff trademarks, long waterlines made even longer when heeled, powerful, broad sterns, and exquisite concave “hollow” dinghy bow sections, defined a new Herreshoff look. It was the Alerion half model “with added wood to represent a full keel and a more raking sternpost with a bigger, deep rudder” that led to the Newport 29 design.1

A visitor to the Herreshoff Marine Museum in Bristol, RI is struck by the lines of the boat sitting right out front: Sadie. My own guess is that the Newport 29 design was actually a scaled-up model of Alerion and this Sadie, a 31-foot sloop built for a local customer in Bristol. Capt. Nat liked Sadie so much that he made a larger version, the Newport 29. Which came first as the source of genius, Alerion or Newport 29? This is still a mystery of the Wizard of Bristol.

In his own letters, Capt. Nat says that after he sailed the 29 he sketched a smaller 26-foot sloop, Alerion, with a gunter rig, for himself to singlehand. That boat sits in the dinghy shed at Mystic Seaport Museum in Mystic, CT. That design was the point of departure for the Nantucket Alerion that sailors so admire in that harbor, with 30 now built in Nantucket and raced since the 1970s.

The Twins live together at Oakcliff Sailing

Team Dolphin, headed by myself and Brian Simmons, a Chicago financier, has raced in Nantucket in the Vintage Day Racer class of the Opera House Cup since 2015, with several podium finishes. We’ve been privileged to sail Dolphin since then, both in classics regattas and the local weekend sailing conducted by Oakcliff Sailing in Oyster Bay, NY. My article from 2015 [“Team Dolphin Takes the Vintage Day Racer Prize in the Opera House Cup” is archived at – Ed.] told the story of the boat’s long, successful history with the Lockwood family, contributing to the claim that she is the “winningest boat” in Northeastern racing history, if not U.S. racing history.

Today, Dolphin’s homeport is Oyster Bay, under the watchful eye of Dawn Riley, Oakcliff’s Executive Director. Since 2015, Dolphin (and more recently Mischief) are part of a 17-boat flotilla of classics ranging from the 26-foot Judy, a 1946 S&S daysailer, up to the 60-foot Rhodes sloop Caper. All of them race on spring and fall weekends in Oyster Bay, presenting a unique opportunity for sailors of any level to sail a classic wooden yacht: pure plank-on-frame. According to Susan Wayne, who chartered our alter ego, Mischief, for the Opera House, sailing the Oakcliff Classics is “the best kept secret in New York sailing.”

Reuniting the Twins for the OHC

We wanted to see both Newport 29s compete, and Susan Wayne jumped at the opportunity to bring Mischief up to the Opera House. We had floated the idea of having the Herreshoff Twins in Nantucket when we heard Oakcliff was acquiring Mischief from her owner in Mystic, CT. The only visible difference between the two boats after 105 years of sailing is the presence of jumper stays on Dolphin’s original spruce mast, and the tiller on Mischief. And what is the story behind that tiller?

Mischief’s crew looks for breeze on Oyster Bay. © Yana Copek/

A History of Mischief, an Appearance of Rogue

As steeped as Dolphin has been in Southern New England sailing, Mischief started as a Chesapeake Bay boat. Delivered with a gaff rig, a photo from 1927 shows a huge 170% overlap genoa with her new Marconi rig. Although not raced as heavily as Dolphin, whose Shelter Island owners the Lockwood family, dominated from the 1940s to the ‘70s, Mischief had her own race record of note. She took first place in the 1931 Bayside-Block Island Race. She vanished south, resurfacing under new owner David Cabot who raced her occasionally.

In 1973, Classic Rating Formula (CRF) founder Chris Wick bought Mischief. He preferred steering with a tiller, so out went the wheel and pedestal. That arrangement turned the cockpit around, placing Mischief’s trimmers in the back of the boat as opposed to Dolphin’s layout with sail trimmers up front, driver in back, and the operator of the running backstays and traveler riding the transom. Wick restored the original tall rig with a new mast and came back in 1985 to take elapsed and corrected fleet trophies in Off Soundings. In spring 2019, Chris donated her to Oakcliff.

On the Opera House Cup scratch sheet was listed “Rogue, Herreshoff.” And who exactly is Rogue? Is she a mysterious, long-lost fifth Newport 29, or an ingenious copycat? A casual observer looking at boats before the start might think there were three identical Herreshoff designs in Class 4 of this year’s Opera House, as there was another boat resembling The Twins.

That mystery boat is Rogue, sailed by Brad Burnham of Fishers Island, NY. Built in 1953 by Seth Perrson from the Newport 29 lines with a rig designed by Sparkman & Stephens in the 1950s, Rogue spent the bulk of her life in Maine and Long Island Sound where her “turboed” bowsprit, taller mast and lower weight made her a light air flyer. Although she’s no triplet – maybe a first cousin – she was about make a splash in the Opera House.

The Showdown

The two Herreshoff sisterships and their cousin squared off on Sunday, August 18 in a virtual dead calm. Dolphin, Mischief and Rogue are not rated identically because of changes made over the years, but they are within seconds of one another. We on Dolphin had to give Mischief 20 seconds per 10 miles, with a typical Opera House course being 17 to 24 miles. Rogue would give both Twins upward of six minutes over 20 miles.

Given the conditions, all ratings were irrelevant. With fluky winds and a shortened course, we never got a real comparison of the boats. The classes starting later had the benefit of more pressure to best their fellow 58 Opera House competitors. On one leg, a reach of 5.5 nautical miles all ended at the first mark in a fog bank. Within the six different start classes, it was positioning at the start and choice of course side that made the difference in finishes.

The start was crucial. Rogue, who turned heads by finishing 5th overall, sailed up the line on starboard and tacked to port when the gun went off. She has a larger rig than the Twins, so had enough momentum to get out from under a stalled OCS boat from the previous start and ahead of the rest of the fleet toward the building wind as others struggled to get to the line. According to skipper Susan Wayne’s account, Mischief found herself in the middle of the start box at the gun and inched herself forward on port. She took seven and a half minutes to finally cross the line, but was on the eastern right side of the course where she wanted to be.


, on starboard, was entangled with the same OCS port boat that Rogue avoided, and with no wind and current running parallel to the line couldn’t free herself to cross the line. We crossed the line after the subsequent class got their prep signal, 10 minutes later.

By going right or north, Mischief and Rogue bet on the current to take them to what at that time was the first mark of the course. Dolphin bet on the incoming breeze and went left. Shortly after their start, the S and C flag were hoisted (the boats that had started an hour ahead of Class 4 still had not reached the first mark) and the finish line was established at the first mark.

A 6- to 8-knot westerly finally picked up, giving Class 5 (12 Metres) and Class 6 (schooners) overall wins in both the Day Racing (12 Metre Weatherly) and Cruising divisions (schooner Eros). Mischief, given time by Dolphin, crossed the fog-shrouded finish line 13 clicks ahead of a fast closing Dolphin; Mischief placed 13th, Dolphin 14th overall.

It seemed fitting, however unsatisfying this first matchup was, that the first known race between the Herreshoff Twins and Cousin came at the Opera House Cup, the granddaddy of the vintage race circuit. These pioneering designs, built as they were as cruisers, have amassed very successful racing careers over their 105 years. August 18, 2019, historical as it was, represented just another milestone in the long, competitive resumé of the Newport 29. ■

1. Herreshoff: American Masterpieces Bray, Mendlowitz, der Linde

Tom Darling organizes Team Dolphin for its annual Opera House Cup sail, and sails Alerions in Nantucket Harbor. He has written articles on Reliance and Dolphin, among other Herreshoff classics.