The Native American Cotochese who lived along the shores of three sheltered bays off Nantucket Sound named them chunkoo, or chunkomuck, skunkomug, or skonkonet. But, no matter what they chose to call them, they pried open the crinkly white shells and found exactly what they were looking for, oysters.

It did not take long for the first colonial settlers, who arrived here in 1639, to learn to relish the seaside delicacy also. And so they named this quiet stretch of southern Cape Cod, Oyster Island Village. In 1648, a delegation led by Capt. Miles Standish negotiated a deed to the area with the Cotochese on behalf of Plymouth Colony, and Oyster Island Village belonged to the English. Later, the townspeople changed the name to Oysterville, and finally, in 1815, they voted to shorten it to Osterville, and so it remains.

Perhaps the most distinctive feature of Osterville is the presence of the Croby Yacht Yard, which is known worldwide for building superior catboats, Wianno Juniors, and Wianno Seniors. Pres. John F. Kennedy's Wianno Senior, seen in photographs across the globe while he was in office, was crafted and stored here. It all began in 1850 when C. Worthington and Horace S. Crosby went into the boatbuilding business on the advice of their father, Andrew Crosby. Actually, it was their father's ghost who made the suggestion to their mother, spiritualist Tirzah Lovell Crosby, who relayed it to her sons.