Thirty Years of Sailing, Stories and Oysters!

“Skipjacks” are everywhere throughout Dorchester County. While most of the actual Skipjack boats have disappeared from the Bay, they have reappeared as logos all over Dorchester County. Skipjack logos are seen on elementary schools, Route 50 shopping centers, motel signs, local company vehicles, and banks.

Skipjacks have permeated our everyday lives, as seen by this sign in downtown Cambridge. Once upon a time, skipjacks drove much of the local economy. Today the skipjack logos establish a connection with those days long ago.

The skipjack, with its large sail, raked mast and low rise, is the perfect subject for a graceful logo design. Skipjack logos, however, have a purpose and are used to establish a connection with this place, harkening back to an era when there was a fleet of skipjacks harvesting the lowly oyster that drove much of the local economy and when everyone knew a waterman, or was one themselves.

“There is no there there,” is a Gertrude Stein quote that is usually used to describe “placeless environments” that have no special relationship to where they are located. A prime example is a strip mall. In contrast, a “sense of place” is an environment where there is emotional connection deeply felt by inhabitants and visitors created by both the tangible features of the environment and knowing how prior generations interacted with it.

The story of the skipjack, and of the watermen who worked on them, how they interacted with the water environment of the Chesapeake Bay, is an important part of what gives the area of Dorchester County a strong “sense of place.”

Prior to the Civil War, very few people made their living harvesting the abundant oyster, there being no way to get oysters to a wider market before they would spoil. It was not until shortly after the Civil War that a combination of factors led to an explosion of demand well beyond the area around the Bay for oysters and which created a local culture that defines this area.

An important factor was the arrival of rail lines on the Eastern Shore allowing the rapid shipment of oysters almost nationwide. In addition, vacuum canning and commercially made ice were now also available, both of which greatly extended the area to which oysters could be delivered. This started the “great oyster craze” when the demand for local oysters nationwide appeared endless.

Toward the later part of the 1800s a boat was needed that could harvest the oysters in the shallower waters as the oyster reefs in the deeper waters were becoming depleted. This led to the development of the “Skipjack,” a boat uniquely qualified to harvest oysters. The relative ease of building a Skipjack, the small number of crew needed to operate it, the ability to pull dredges under low wind, and its shallow draft, soon made this boat the preferred vessel to harvest oysters to meet an unlimited demand. At one time, there were over 700 skipjacks on the Bay, making it the iconic boat for this area. Today, only a handful of the iconic boats ply the Chesapeake Bay.

Thirty years ago, a group of individuals were concerned that Dorchester County would lose an important part of its cultural heritage, it’s “sense of place,” if there were no tangible reminders of the important part that working on the water played in the history of Dorchester County. They created the Dorchester Skipjack Committee with the intention of building an oyster harvesting skipjack. Currently, the skipjack that they built 30 years ago, the Nathan of Dorchester, is used for public and charter cruises with docents telling the story of the oysters of the Bay and the many people who made their living harvesting them.

Making a living as a waterman harvesting oysters, however, is very different than taking a sunset cruise on the Nathan. For starters, oystering is mostly done during the winter months. Making a living working on a skipjack, a waterman would need to leave the dock long before sunrise to arrive at the oyster reef by sunrise, the time when dredging could start. Getting to the oyster reef during the winter would often require maneuvering around ice floes in the dark and unfurling sails in freezing rain. Before the introduction of diesel engines at the turn of the century, dredges weighing hundreds of pounds were hauled up by a manually operated windlass. Oysters would be dumped on deck to sort out, setting aside the good ones from those that were dead “boxes” and shoveling them into piles.

The danger of slipping on an icy deck and going overboard in icy water weighted down with heavy oilskins, the dismemberment that could result from a cable on the windlass breaking, the possibility of infection from getting cut by a sharp oyster shell, the monotonous food consisting mostly of beans and oysters, and the threat of dangerous winter storms on the Bay made this an unattractive occupation for most landlubbers.

The overall shortage of labor during the “Great Oyster Craze” found captains often resorting to going to Baltimore and scouring the dives and bars for potential crew. An official report from 1879 describe dredgers as “perhaps one of the most depraved bodies of workmen to be found in the country…As may be supposed, the life led by these men on board of the vessels is of the roughest kind, hour after hour winding away at the windlass, pulling on a huge dredge, or else stooping with backs nearly broken culling oyster.” It is these workmen however that brought up the oyster “gold” from the bottom of the Bay around which much of the local economy was dependent.

It is important to know both the good stories and the not so nice stories to fully appreciate our relation to this area’s environment and to make us aware of what we need to do to preserve it for the future. The Nathan of Dorchester has been telling the stories of this place for the past 30 years and will be celebrated on July 4, the 30th Anniversary of its launch, with a celebration and rechristening at Long Wharf in Cambridge at 10 a.m.

For more information or to book a two-hour sail on Saturday, June 1, 8, 15, 22, or 29 or a Third Thursday Sip ‘n Sail on June 20, visit Custom charters are available as well; email

~ Written by David Rose who serves on the 30th Nathan Birthday Committee.

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