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Magnus Kullberg
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October 13th, 2025
Photography © Chesapeake Bay Maritime Museum
^ Skipjack HM Krentz cruises the Miles River
Generations of watermen carved a living out of the beautiful Chesapeake Bay. By far the best known of the boats they used is the Chesapeake Skipjack, so called for their unique design with vertical hull sides and flat bottoms resembling the Skipjack tuna that leaps out of the water. Rugged yet graceful, they were built for oyster dredging in the shallow waters of the Bay and were both workhorses and symbols of an era in the nineteenth century when the oyster industry thrived. Skipjacks are now seen in very much smaller numbers, symbols of that earlier time and the traditions of the Chesapeake Bay watermen.
^ Skipjack Rosie Parks is part of the floating fleet of traditional Chesapeake vessels at the Chesapeake Bay Maritime Museum in St. Michaels, MD
In the 1890s Chesapeake Bay was at the epicentre of the global oyster trade. In those days, large two masted vessels called Bugeyes were used for oyster dredging, but they became too expensive and cumbersome to operate. Enter the lovely Skipjack which was cheaper and easier to build yet could still manage heavy oyster dredges. With a single mast, they were easier to run and perfectly suited to the conditions in Chesapeake Bay.
^ Using an oyster knife to demonstrate how to shuck a Rappahannock river oyster | Jennifer / stock.adobe.com
The Skipjack fleet quickly expanded with many small boatyards building them, as well as the watermen themselves in towns across Virginia and Maryland. Mission central were the towns of Deal Island, Crisfield, Cambridge and Tilghman Island. By the early 1900s over 1,000 Skipjacks were in the water dredging oysters and they were the rump of the oyster fleet.
^ Waterman taking a break on a skipjack boom above a pile of oysters, Magothy River Anne Arundel, MD, 1969 | Photograph by Robert deGast
Perfectly designed for their task, with shallow draft – often less than 3 feet, their wide beam made them stable and perfect for work in the shallow waters loved by oysters. Normally the hull was V-bottomed or hard chined so that the boats could dry out on the seabed when unloaded or moored.
^ Skipjack laden with oysters on the Chesapeake Bay, 1969 | Photograph by Robert deGast
The engine of the Skipjack is a large mainsail and jib on a long bowsprit. Her decks had lots of space for the watermen to move around when sailing the boat and for oyster sorting. Their dredging equipment was often manual, unless they had a winch to haul up the heavy iron dredges full of oysters.
^ Skipjack Martha Lewis underway, 1969 | Photograph by Robert deGast
Many of the fleet also had pushboats which were motor powered and tied to the stern, legal in Maryland for navigation but not to be used whilst active dredging was underway.
The oyster season was from November to March, when the Bay was cold and windswept, and so conditions for the watermen were harsh. They were normally crewed by a Captain – often the boat’s owner – and carried between three and five deckhands, normally family members. The boats would be working from before sunrise to the last of the sunset.
^ Skipjack Han Em Harv competes in the 2021 Choptank Heritage Skipjack Race | Photograph by George Sass
Physically hard work, the heavy dredges were dropped and then hauled back by winch or manually. Once aboard, the oysters were cut from the mud and shelled right there on deck. They were then sorted by size and quality and stored in wooden bushels (volumetrically 8 gallons) to be sold at market. It was this oyster harvest that supported the watermen throughout the year.
At its peak, the Bay’s oyster industry supplied almost half the planet’s oysters and of course the Skipjacks were central to that success.
Overharvesting became an increasing problem, so Maryland State passed new laws banning motor powered dredging and only allowed sailing Skipjacks to dredge oysters. Therefore, the Skipjack was not only traditional for the watermen but they were also a commercial necessity and they continued to dredge for oysters under sail into the 1980s. This made them the last commercial sailing fleet in the United States. After this the oyster population collapsed because of over fi shing, habitat destruction and disease.
^ A group of skipjacks, including the Annapolis Maritime Museum’s Wilma Lee, compete in the 2021 Choptank Heritage Skipjack Race | Photograph by George Sass
Today there are fewer than twenty Skipjacks surviving from the original fleet of over a thousand. Some look very sad, whilst others have been restored for education as well as tourism use. These lovely boats have found support from:
You can see them at the annual Skipjack Races at Deal Island and Tilghman Island. This is a chance to celebrate these brave little boats and the watermen who sailed them.
Maryland designated the Skipjack as their State Boat in 1985 – the only state to recognise their important place in the culture and history of Chesapeake Bay.
Skipjacks may now be seen giving service as floating classrooms and to demonstrate the fabric of Chesapeake Bay down the generations. They are used to educate students and the public about the Bay’s ecology, history and also about the environmental challenges that we all currently face.
^ A scene from the 2015 Deal Island Skipjack Races
Authors, photographers and artists are still drawn to their sweet lines and their extraordinary history and that of the watermen who operated them.
Mention Chesapeake Bay, and it is not long before someone will mention the Skipjack which is synonymous with its waters. A thoroughly locally born boat built by those who lived on the shores of the Bay and operated by them too, where sailing power and not motor power was the only propulsion method available. We also remember the thriving oyster beds and a time of plenty before disease and overfishing destroyed the industry.
The push is now underway to restore the once-mighty Chesapeake Bay oyster beds, as Skipjacks have disappeared from the working fleet. However, they continue to sail on as guardians of the Bay’s maritime legacy. Restoring and preserving the remaining members of the Skipjack fleet means that this piece of America’s history is also preserved, together with the memory of the hardy watermen who built them, sailed them and eked a living from their wide decks.
^ The Chesapeake Bay Maritime Museum’s 18-acre waterfront campus includes the 1879 Hooper Strait Lighthouse
A massive Berthon thank you to the Chesapeake Bay Maritime Museum (CBMM) for their help with this article and for allowing us to use the wonderful Skipjack imagery illustrating this piece.
CBMM is located along the Miles River in historic St. Michaels, Maryland, United States.
It explores and preserves the history, environment and culture of the entire Chesapeake Bay region, and makes this resource accessible to everyone.
Not only that –
CBMM’s Members-Only Marina offers 55 slips with full amenities. Visit: https://cbmm.org/docking-at-cbmm/
CBMM’s Charity Boat Donation Program accepts and sells well-maintained boats year-round to support its mission. Learn more at: https://cbmm.org/buy-a-boat/
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