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In Fall 1913, a group of sailing enthusiasts on the southern coast of Cape Cod (Massachusetts), all members of the Wianno Yacht Club, asked Manley Crosby, of Crosby Boat Building Storage Company, Osterville, to build a small racing daysailer, suitable for the difficult local conditions, characterized by strong winds and tidal currents and frequent unmarked sandy shallows. This is how the Wianno Senior “Knockabout” came into being, named after the small village of Wianno, so called from the  native American chief of the Iyanough tribe from whom the area had been bought by the first settlers in 1664.

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The Wianno Senior met expectations from the very beginning, as shown by a 1915 review in the specialized journal, The Rudder: “In performance, the new boats have fully come up to their requirements. They have shown themselves able, stiff and seaworthy, they mind their helms like obedient children and take sound waves without plunging or “slapping”. In speed they have been an agreeable surprise, for in a series of Interclass races pitted against boats designed by Herreshoff and Lawley they they were able to hold their own, except in the very lightest of winds."

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This gaff rigged sloop became the boat on which, for almost a century, generations of New England families raced every summer weekend in the waters of Nantucket Sound, off the southern shores of Cape Cod: the most famous was certainly the Kennedy family

In the early 1930s, despite the Great Depression, the fleet had more than 60 boats. In 1946, with over 100 boats in circulation, a Class Committee was founded to ensure uniformity in construction and promote racing.

This let the Wianno Class race successfully without changes until the Spring of 1976 when the last three wooden Wianno Seniors were launched and the old Crosby shipyard was sold.

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To avoid the Wianno Seniors disappearing from the history of yachting, members of the Class with the help of other organizations and private donations, commissioned the office of “Sparkman & Stephens” to engineer the Wianno Senior for fiberglass construction, while maintaining characteristics and performance of the wooden boat.

The first two fiberglass Wianno Seniors were launched in 1986, keeping the appearance, the weight and stiffness, the fittings, the spars and the deck equipment of the wooden Seniors unchanged. In subsequent years, the results of the Scudder Cup races (the local Wianno Senior championship) showed that boats in fiberglass had the same performance as the wooden ones, and were not necessarily superior.

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In the winter of 2003, a terrible fire struck the storage shed of the Crosby's shipyard in Osterville, destroying 21 Wianno Seniors, 18 old wooden and 3 mor recent fiberglass boats.

What could have been a serious blow to the Class led instead to an almost total renewal of the fleet as most owners who lost their boats that day ordered new fiberglass Wiannos. To date, over 220 boats have been built. Of these 50 are in fiberglass, including 7 in Italy.

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