Seaside Stories

Museum brings history of Osterville boat-building to life

By Amanda Wastrom

With 15 boats whose collective history spans the 20th century, the Osterville Historical Museum houses the most extensive collection of small and large wooden boats in the state of Massachusetts. The collection focuses on boats with a strong tie to the village and to the history of Cape Cod recreational sailing. Recent acquisitions include the Gypsy, a turn-of-the-century racing catboat on the National Register of Historic Places, and the Eagle, a Jersey sea skiff owned by the local Van Winkle family—a familiar fixture at the Wianno Yacht Club dock for decades before it was donated to the museum last year.

The museum also houses 13 boats built by the Crosbys, arguably the most famous boat-building family on Cape Cod. Jesse Crosby established a boatyard in Osterville in the late 1700s and the family has carried on the tradition ever since. The Crosby story parallels the Cape’s broader history, as it became a bustling hub of maritime activity in the 19th century. “In the 1850s, you either went fishing or built boats,” says museum director Jennifer Williams. “The Crosbys were the boat builders du jour of Osterville.”


A touchscreen at the Osterville Historical Museum

In the early 20th century, as tourism and seaside recreation replaced dying maritime industries like whaling, fishing and salt making, the Crosbys solidified their reputation by building fine recreational sailboats, such as the catboat and the Wianno Senior. Wealthy families like the Du Ponts and the Mellons were instrumental in commissioning new boats and keeping the boatyard busy year-round. “For these families, sailing was integral to their daily existence,” describes Williams. “Women would walk along the groves near the Wianno beaches and watch the afternoon sailing races. It was very much part of upper-class society.”

Each Crosby boat in the collection highlights a different part of the family’s story. The Cayuga, a catboat built by Horace Manley Crosby in 1922, is the oldest Crosby boat in the collection. Williams describes it as “the pillar of the Crosby’s boat-building legacy.” Originally built as inshore fishing vessels, catboats were uniquely suited to Cape Cod waters. With a deep, wide hull, barn door rudder and forward mast, the Cayuga was built to be maneuverable and unsinkable, resilient enough to ride out a nor’easter. Given its age (94 years old), the Cayuga is also a testament to the durability of fine craftsmanship.

The Venture, a Wianno Senior built in 1935 by Max Crosby (who consequently worked on every Wianno Senior ever built by the family), represents the second marquee Crosby design. The Wianno Seniors were designed by Horace M. Crosby as a 25-foot day sailor specifically for racing in Nantucket Sound’s stiff winds and choppy surf. Made famous by the Kennedy family, this class of wooden sailboats has captured the wistful heart of many sailors. “If you have ever sailed a Wianno Senior, you know that it takes a hardy group of sailors to handle it,” says Williams. “For those who can, it is the essence of sailing.” First built in 1914, the Wianno Seniors were (and still are) the one-design racing boat for the Wianno Yacht Club in Osterville. These boats are still a very active racing fleet with annual events at Bass River, Edgartown, Hyannisport and Wianno.


One of the youngest Crosby boats in the collection is Little Cloud, a Cotuit skiff built by Edward M. “Ned” Crosby Jr. in 1994-95. Originally inspired by the flat-bottomed skiffs used by Cape Cod oyster and clam fishermen, the Cotuit skiff has the distinction of being one of the oldest continuously sailed fleets of one-design racing boats in the world, with the first races run in the bays between Cotuit and Wianno in 1906. The boats are infamously challenging to sail and easy to capsize. Little Cloud was the first wooden boat that the eighth generation Crosby built on his own.

Little Cloud_2006

Little Cloud

While the family no longer owns the boatyard in Osterville that bears their name, many members of the family still carry on the tradition. Ned has been building custom wooden boats out of his shop, E.M. Crosby Boatworks, in West Barnstable, since 2001.

The beauty of historic preservation lies in the repurposing of these antique boats. Once their sailing days are finished, they become storytellers. And oh, how the stories are endless! “You don’t have to be a sailor to fall in love with these beautiful wooden boats,” says Williams. “From their names to their stories to the craftsmanship that went into them, they really do take on a life of their own.”

While a visitor cannot experience each boat exactly as it was when it was under sail, the museum aims to recreate the sights, sounds and smells of the boat-building process. “It really is that colonial-era method of building boats,” explains Williams. “A lot has changed, but these boats are still made the same way. Everything from putting the planks in the steam box before they are formed on the mold—the materials, the processes—some of the tools are over 100 years old!”

Many of those tools and an extensive collection of Crosby half-hull models are on display at the museum, where Herbert F. Crosby’s boat shed sits in the middle of a long string of barns and buildings that house and protect the boats.

It is a touchstone of the museum’s mission to preserve and share each boat’s individual story so that perhaps, as you are standing there, admiring the Venture’s elegant silhouette, you can imagine that the wind drifting in from the open barn door is really the same offshore breeze pulling you out into Nantucket Sound.

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