The skipjack Rebecca T. Ruark, right, competes in the 59th annual Skipjack Races in Deal Island, Md., on Sept. 3, 2018. It is the winningest skipjack in the race’s history, having won its 11th race in 2016. (Photo by Joan Smedinghoff/Chesapeake Bay Program)

Skipjacks are a quintessential Chesapeake Bay boat. While its exact origins are unknown, they first appeared in the late 1800s and are now associated with the waterman community of Deal Island, Md., in the Tangier Sound.

The skipjack is a boat for oystermen. Its sails were designed in a way that didn’t need much maintenance while at sea, so workers could focus on hauling oysters over its characteristically low sides, which aided in that effort.

It’s also meant to be easy to build. Instead of requiring detailed blueprints, a skipjack is built on ratios, and its overall size depends on the height of the tree—or later, telephone pole—that would make up its mast. Using the mast, you can figure out the length of every other major component of the skipjack. For example, the length and width of the boat add up to the height of the mast. The boom, the long wooden piece that runs parallel to the boat and helps hold the larger sail, should be the same length as the deck. This made it easier and less expensive to build, and at one point these boats filled the marinas in watermen communities around the Bay.

Today, about 30 skipjacks remain on the water, and even fewer still function as workboats. However, the skipjack is so iconic in the Bay that in 1985, it was designated the state boat of Maryland.

To keep the waterman and skipjack culture alive, Deal Island holds the annual Skipjack Race and Festival around Labor Day, now in its 59th year. The race and festival give outsiders a glimpse into a culture that may not be around for much longer.

This year, the skipjack Ida May took first place for its second year in a row. Captained by Shawn Ridgely of the Chesapeake Bay Foundation, this is the third time the boat has won the race since it was restored by owner Gordon Gladden of Salisbury and his brother Elbert.

Learn more about the connection between Deal Island and the skipjack.



J. Brooks


Clawing oysters from the bottom,

they sail the Chesapeake bay.

They're hard sided with simple rigging,

but yare in their own unique way.

An office for hard-working watermen

for well over one hundred years,

they've sailed these fickle tidal runs

mindless of weather and fears.

Their hulls are V-shaped and wooden

with a hard chine and square stern.

They’re fat as a walrus across the beam,

and handlin’s a craft to be learned.

The mast is a log without spreaders;

it’s stepped towards the bow of the boat;

a retractable centerboard fixed in her keel

will keep her off bars and afloat.

A curved longhead under the bowsprit

sports bright-painted, carved trailboards.

She’s fifty feet long from her bow to her stern

with a figurehead mounted up for’ard.

She’s made to work these shallow waters,

but should she fetch up on a shoal,

there’s a smart little dingy abaft the helm

to push her off or take you home.

JB 1993

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