Sharpies are long, thin sailboats with plane bottoms, enormously shallow draft, centerboards and straight, flaring side. They are assumed to have originated in the New Haven, Connecticut area of Long Island Sound, United States, for the oystering industry, which thrived in New Haven harbor with its wide, shallow waters.
The type is believed to have evolved from the Native American trench canoes that were initially used in the area. European setters changed the original dugout form so that the sides and base were flat, to improve steadiness and hauling capacity.
It was around 1840-1850 that the initial true sharpies were being built in the New Haven area. These were long boats, approximately 27 feet or so, crewed by one man and rigged as a cat-ketch, with three mast steps; one at the bend over, one amidships and one in between. In light whether, two masts would be stepped at the duck and amidships, but in heavier weather, a single mast would be stepped in the middle. Larger models, up to 35 feet, were crewed by two men. The New Haven models were typified by plumb bows with the base just out of the water and surrounding, counter-sterns.