The Crosby family’s legacy of boat building in Osterville

Photography courtesy of the Osterville Historical Museum

If the catboat were an actual cat, one would think she’d be an indoor variety—sure of her surroundings, comfortable, given to sunbathing and leisure—and she’d be round, ample, a far cry from a svelte Siamese. One of the design principles of these boats is that their beam, or middle part, is proportioned at half the distance of their overall length. That’s a big ball of fur. Yet, the boat was built to stand up to the stiff southwest breezes of Nantucket Sound, and its name derives from its agility, not its shape. Back in 1850, when the very first catboat appeared on a racecourse in Osterville’s North Bay, a boat yard worker exclaimed that the stout, 22-foot boat “comes about quick as a cat.” This moment would not only lead to the naming of a new sailboat classification, it would also serve as the birth of an icon of the Cape and Islands, and it would accelerate the elevation of one local boat building family to international renown and acclaim.

The Crosby family has been building and maintaining boats in Osterville since 1744, when Jesse Crosby, at age 11, started working as a carpenter’s apprentice for his uncle, Jesse Lewis Crosby. Their work included boat building, but it was Jesse’s sons who opened and operated the family’s first boat yards in Osterville, where Daniel Crosby’s shop would build over 75 boats. Andrew Crosby, a grandson, planned the first catboat; though he died before its construction, his vision would carry from beyond his grave.

As Captain Herbert F. “H.F.” Crosby related in the July 1928 issue of Motor Boating magazine, Andrew had been on a voyage when he first spotted a boat with a centerboard, a rectangular piece of wood that swings down into the water on a pivot at the center of a boat. Sailors lower the centerboard in deeper water to help the boat sail straight and displace weight from the full sails; in the bays of Osterville, one can raise the board and skim above sandbars without running aground. H.F. recalled, “Grandfather [Andrew] died when my father, Horace, was thirteen, an’ when uncle Worthington was sixteen. Within a few months the two boys decided to build a boat. … Naturally she had to be shoal draft, and they thought they’d try to build one of those centerboards they’d heard their father speak about. But they didn’t know how to go at it.” The boys consulted their mother, Tirzah, for advice, but the answer would come from their deceased father’s spirit. H.F. stated, “She didn’t say a thing at first, but just looked and looked at her little sewing stand. When the stand began to rock and to shake she said, ‘Yes, boys, a centerboard would be all right.’ Every time those boys were in a difficulty with that first boat, they’d go to their mother an’ she’d consult that little stand of hers. If the stand rocked it meant, ‘Yes, go ahead,’ an’ if the stand didn’t move it meant ‘No, you’re on the wrong track.’ They believed that their father was directin’ them through their mother. They believed it, an’ she believed it, an’ I believe it.” Another version of the story holds that Tirzah invited a spiritual medium to conduct a seance in their home, but regardless of details, in the family’s history there is no doubt that Andrew’s spirit guided his sons as they crafted their revolutionary new boat.

While the Crosbys built many of the early catboats for utilitarian purposes such as fishing and clamming, the industrial revolution led to the establishment of summer communities that centered around leisure activities. Yacht clubs formed, and members raced their sailboats. Around the turn of the century, partially inspired by the success of boat builder Nathaniel Herreshoff’s move to standardize some of his boats into “one-design” classes, members of the Wianno Yacht Club approached Horace Manley Crosby, younger brother of H.F., about creating a fleet of racing sloops. Sailboat racing had been growing in popularity but also in complexity, as race committees concocted handicap systems to score contests between vastly different boats in a fair manner. A one-design, in which each boat conforms to strict, identical specifications, would simplify scoring and lead to more uniform competition. In theory, one-design racing ensures that the most skillful sailors will most consistently win, a merit-based concept that probably aligned philosophically with many of the nation’s preeminent capitalists who had adopted Osterville as their summer home. To fulfill this rising demand, H. Manley Crosby launched the first fleet of Wianno Seniors, 14 sleek racing sloops, each 25 feet in length with a centerboard that lowers down through a shallow keel. He surely had no way of knowing that his design would outstrip even the catboat as a classic sailing vessel, one that four years ago would celebrate its 100th anniversary.

C. Worthington “Uncle Worthington” Crosby and some of his crew are photographed outside of his boat shop around 1890. In the front row are: J. Milton Leonard, Warren Lovell, Uncle Worthington, and Alexander Bacon. In the back row are: Charles E. Lewis, Ralph Crosby, H. Manley Crosby, Harold Crosby, Oliver C. Coffin, Joseph C. Crosby, Billy Granger, Wilbur Crosby, and Charles A. Hall. The two boys in the back are unidentified.

The success of Wianno Seniors racing in West Bay and off the shores of Osterville led to fleets springing up in other yacht clubs, such as Bass River, Stonehorse and Hyannis Port. An interclub series, the “Scudder Cup,” formed, and despite the comings and goings of different clubs, it remains the most prestigious summer racing event on Cape Cod today. However, the success of a young senator from Hyannis Port would propel the class to truly mythical status, for when photographers captured John F. Kennedy sailing with Jacqueline and their children, the Wianno Senior raced around the world and into America’s history books and hearts.

In addition to building boats, the Crosby companies enjoyed reputations for excellence as full-service boat yards. At one point, six Crosby yards ran simultaneously, but by the 1950s, they had consolidated into two: Crosby Yacht Yard and Chester A. Crosby & Sons. Eventually, both entities sold outside of the family, but both continue to operate today, with Chester A. Crosby & Sons renamed to Oyster Harbors Marine. Chester “Chet” Crosby also introduced new technology that would greatly facilitate the upkeep of the Wianno Senior fleet. In a 1987 issue of Cape Cod LIFE, Chet recalled, “I saw there was a demand for a way to haul out the Seniors, to paint and clean them. In 1926, I put in the first marine railway in Osterville. In succeeding summers, I was overwhelmed with the amount of work I got.” According to Jennifer Williams, curator of the Osterville Historical Museum, the boat yards also worked with the Army Corps of Engineers during WWII. She says, “They trained mechanics for amphibious craft, the duck boats, to prepare for the D-Day invasion. A huge contingent of soldiers lived in a camp on the golf course nearby.”

At the Osterville Historical Museum, “Home of the Crosby Boats” is, among other things, a testament to the life works of eight generations of Crosby boat builders. A series of interconnected boat sheds houses the largest collection of wooden boats in Massachusetts, which showcases the family’s craftsmanship and art. Williams notes that when Bill Koch built Nauticus Marina, he donated H.F. Crosby’s original shop to the museum. She says, “The tools, the work benches, they’re all there, along with the hull of one of the boats.” Also in the shed is H.F.’s wood stove. “This is a key part of the Crosby story,” Williams explains. “The Crosbys built using a colonial method—they carved half-hull models, then extrapolated from there to construct the full-sized boats. If they didn’t like the model, they’d throw it in the stove and start fresh.”

In addition to beautifully restored wooden boats, the museum exhibits more tragic pieces of Crosby history. Behind H.F.’s shed are the remains of an old cat named Lazy Jack. The boat is rotting apart, but the museum keeps it as an example of what happens when people neglect wooden boats too long. The museum also displays the charred remains from when, in 2003,  Crosby Yacht Yard’s large wooden storage shed burned to the ground. Fortunately, there were no fatalities, but 21 Wianno Seniors went up in flames. Some feared that the fire would spell doom for the fleet, but the sailing community rallied; while one can never truly replace a family boat, new fiberglass Seniors were built, and the fleet is healthy and robust today.

As the Osterville Historical Museum preserves the Crosbys’ past, Chet’s grandson, Ned, has been busy tending to the present and future of the family legacy with his E.M. Crosby Boatworks. Ned, who began his career at age 7, when his grandfather hired him at $2/hr. to sweep the yard, spent 11 years working in Chet’s shop before heading off to college in 1987. He learned every facet of the boat yard, from rigging to maintenance to building. Since launching E.M. Crosby Boatworks, Ned has built and restored a number of wooden boats—including dories, Cotuit Skiffs, other sailboats, and the Crosby 38, a wooden “express cruiser” motor yacht that won “Best Professionally Built Powerboat” at the 2011 WoodenBoat Show’s “Concours d’Elegance” in Mystic Seaport. In 2010, the Wianno Senior Class Association offered Ned a license to build new boats, an honor that he “eagerly accepted.” E.M. Crosby Boatworks and Crosby Yacht Yard are the only two boat builders to hold this license.

Currently located in West Barnstable, E.M. Crosby Boatworks will move back to Osterville in the summer of 2019, to a location on the water across from the old yards. Ned explains, “We’ll be right over the bridge, where my father’s workshop was, which also doubled as the Coast Guard Station.” In addition to bringing the Crosby family back to Osterville’s shores, a cause for much elation at the Historical Museum, the move will fulfill both practical and personal goals for Ned and his family. “It will be so much easier for us to rig and launch boats; being on the water will provide us with efficiency,” he says. “And it will be neat to have my four daughters grow up there, to experience what I experienced as a kid.” In the process, the Crosby homecoming will provide a similar service for a wider family of boaters, pleasure sailors and Wianno Senior racers—it will allow us all to take part in a legacy that stretches over 240 years.