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What is a Skipjack?

The "skipjack" is a unique type of commercial wooden sailing vessel, used for more than 100 years to dredge oysters from the Chesapeake Bay. Launched in 1994, the Nathan of Dorchester is likely to be the last skipjack ever built to be a sailing dredge boat.


The style of working sail boat known as the "skipjack" evolved in the late 1800s as a result of the increased demand for Chesapeake oysters. Better road, bridge and rail networks allowed greater range for fresh oyster markets and New England harvests were shrinking. In the mid-1800s, oysters were collected by hand (tonging) on small fishing boats, and by hand- or mechanically powered dredges on schooners–round-hulled, deep draft, two-masted vessels–and modified Bay freight schooners such as pungys and bugeyes.

At the height of the oyster harvest period in the late 1800s, there grew a need for shallow-draft sailing vessels for dredging, that had a low freeboard (deck close to the waterline) to ease hauling in the dredges, that were easier and cheaper to build than the schooners, and that required fewer crew for operations.

Answering the need was the development of a larger-scale version of a small, single-mast boat with two sails being used by watermen at the time for dredging for blue crabs in the shallow grassy reaches of Bay tributaries.

Caleb Jones
Skipjack Caleb W. Jones
under reconstruction,
showing V-bottom and frames

Alternatively, Marine surveyor Frederick E. Hechlinger suggests that the design may have first been introduced to the Bay by Baltimore oyster packers, who were originally from Connecticut, where a similar vee-bottomed type of boat had evolved.

The origins of the name are obscure, but probably refer to a fish of that name, a type of bonito tuna. Hecklinger surmises that a V-bottomed boat was built and named "Skipjack" after the fish, and was subsequently imitated, with the type eventually aquiring the name.

Designed For Power

Whatever the origins, major boat builders on the middle and lower Eastern Shore of Maryland began to build these modified sloops with a sharp chine and shallow, dead-rise hull with centerboard. The single raked mast was placed well forward and the sharp bow was extended with a bowsprit, allowing the boat to carry a large main sail giving enough power to haul the big oyster dredges, and a self-tending jib, allowing crew to concentrate more on dredging.

Typically, the configuration required the length of the boom to equal the length on deck, the length of the bowsprit to equal the width of the deck or "beam" (1/3 the length on deck), and the mast height to equal the length on deck plus the beam.

Caleb Jones
The Nathan of Dorchester's trailboard and eagle,
carved by Harold Ruark

Builders and owners of these graceful, powerfully driven sailing vessels decorated them with carved, brightly painted trailboards, bearing the boat's name, and carved figure heads under the bowsprits.

Skipjacks generally ranged from 30 to 60 feet on deck and could carry 100 to 500 bushels of oysters. The Nathan is a medium-sized skipjack, built to carry about 200 bushels.

With the development of the gasoline engine, the rowing dinghy typically hung on the davits at the stern was powered with a two- to four-cylinder engine. This enabled the skipjack to have a power source–a "pushboat" or "yawl boat"–in the event of light wind conditions.

Setting Limits

Caleb Jones
Skipjack Hilda Willing's dredges

As a result of early attempts by the State of Maryland to conserve the oyster beds, regulations were passed to limit the use of the pushboats to going to and from the oyster dredge areas. Skipjacks were required to do the actual dredging only under sail, with the pushboat hauled up into the davits as evidence of compliance.

It was not until the 1960s that the regulations were eased to allow watermen to dredge under power two days a week, Monday and Tuesday. That was good news as long as the wind was favorable the rest of the week! It was not until the late 1990s that regulations were changed once again, and remain in effect today, permitting watermen to choose which two days they will dredge under power.

As a result, most dredging by skipjacks is done today using pushboats, much more efficient in most weather conditions than working under sail.

The dredging season for skipjacks is from November first to April first, with a current limit of 150 bushels per vessel per day.

An Uncertain Future

Caleb Jones
Skipjack Esther F
Gone, but not forgotten.

Of the original 600 to 800 skipjacks built as dredge boats, mainly between the late 1890s and mid-1900s, only about 20 are still afloat. Of these, only about half a dozen dredged commercially in the past five years. These vessels constitute the last working sail fleet in the United States and are listed on the National Register of Historic Sites. In 1985, the skipjack was designated the State Boat of Maryland.

Unfortunately, even the near-term future of the commercial skipjack fleet is under threat. Over the past 50-plus years, pollution and diminshed oyster habitat due to the ever-increasing human population, have combined with diseases and overharvesting to devastate the oyster beds in the Bay and its tributaries. The result is that we may be witnessing the closing chapter in the colorful history of the Chesapeake Bay's traditional skipjack fleet.

The good news is that there are dedicated individuals and organizations determined to keep these boats alive. Several skipjacks, like Caleb W. Jones shown above, Rosie Parks and Ida May, have been restored in recent years and are back underway. Others are currently undergoing major restoration or repairs, including Kathryn, Helen Virginia and Martha Lewis.

With support from friends, donors and volunteers, we can still save these remarkable boats from disappearing into history.

[Photos courtesy of Cyndy Carrington Miller, The Last Skipjacks Project]