The Willie L. Bennett Skipjack model is a typical medium size built in 1899 in Inverness, once a small town in Somerset County, Maryland. The design is very appealing and is similar in size and general appearance to skipjacks which have survived and are remaining today. At the peak of building, around 1910, there where some 2,000 Skipjack sailing the bay.
The Skipjack evolved because it was simpler and less expensive to construct than a round bottom boat like a bugeye. The hull structure on most Skipjack is fairly typical but since no construction plans were used there were slight variations. Another noted characteristic of the Skipjack as well as many other bay sailing craft is the clipper-type bow with its long cutwater stem, hogged bowsprit, and decorative trail boards.
The Skipjack is the last sailing craft developed on the bay for commercial operation. While the large early fleet has dwindled to about 39 remaining boats, they are still operating for a good reason.