Youth at helm of Nathan of Dorchester

Veena Yarlagadda of Ashburn, VA, was one of the first passengers on the skipjack Nathan to try her hand at the wheel. 

A skipjack tacked up and down the Choptank River in Maryland for two hours on an azure afternoon in late spring. One of the last of its kind still cruising the Chesapeake Bay’s waters, the Nathan of Dorchester returned to its slip with a brimming haul.

Not of oysters, mind you. That’s so 19th century.

This boat was built in 1994 with a different purpose in mind. On this trip, it carried 19 people — not counting its captain and six crewmembers — out for an exploration of a heritage that is disappearing and this particular skipjack’s place in it.

“They said there were so many skipjacks in here you could walk from one side of the creek to the other without getting wet,” Charlie Rouse told the passengers as the Nathan eased into the mouth of Cambridge Creek at the outset of the journey.

Tour on the Nathan of Dorchester

Volunteer Charlie Rouse shares the story of the skipjack Nathan and maritime history on the Chesapeake Bay. 

Skipjacks were once the workhorse of the Bay’s oyster industry. After its introduction to the Chesapeake in the 1880s, skipjacks numbered as many as 1,000 at their height around 1900; today, only about 20 remain. The Nathan has the distinction of being the youngest — and perhaps last — member of that iconic armada.

To spend a pair of brief hours aboard the vessel, with a salt-tinged breeze teasing its two sails, is to peek into a past that continues to shape life in and around the modern Chesapeake Bay.

July marks the 25th anniversary of the Nathan’s launch. The nonprofit that runs the commercial charter service offers two-hour sails on most Saturdays from May to October and one-hour trips on one Sunday per month. It is also available for special events and private outings.

After paying the captain’s wages, all proceeds go toward the maintenance and operation of the 60-foot vessel. (The Dorchester Skipjack Committee reported about $30,000 in receipts in 2017.) The crew consists entirely of volunteers.

There’s also a docent on board. On this particular Saturday, that duty fell to Rouse, an amiable former drug and alcohol counselor from Baltimore. Smitten with James Michener’s 1978 tome, Chesapeake, he retired to the Eastern Shore community of Cambridge, one of the principal inspirations for the book’s fictional setting.

His audience consisted of one sprawling family group and a smattering of couples. Once the boat was under way, so was Rouse, giving a lively recap of the Nathan’s origin story intertwined with snippets of local maritime history.

The skipjack’s home port is Cambridge’s Long Wharf, a marina on the Choptank just a few hundred yards downstream from the Route 50 bridge. If there ever was a capital of Maryland’s seafood industry, this town certainly would have been a candidate. Nearly half of all the 2,000 skipjacks that ever sailed the Chesapeake were built right here, Rouse pointed out.

Oysters on the Nathan of Dorchester

Passengers watch as the crew of the Nathan catches oysters with a cage-like hand scrape from the bottom of the river. In the past, skipjacks were the power behind oyster harvesting in the Chesapeake, using mechanically operated dredges on both sides of the hulls.

Skipjacks are the last sail-powered commercial boats still active in U.S. waters. Their continued existence owes less to romanticism than to a quirky conservation law. To keep oyster beds from getting overfished, 1800s-era lawmakers in Maryland restricted dredging to vessels powered only by sail. That law was later amended to allow a skipjack to get a motorized assist two days a week from a “push” or “yawl” boat mounted to its rear.

Power dredgers vastly outnumber their wind-powered counterparts these days, but state regulations continue to cast favor on the historic fleet. Commercial skipjacks may harvest up to 150 bushels a day; a power dredger can only keep 24.

“Comin’ about! Ease the jib,” Doug Macnair, the skipjack’s captain, called out to his crew several times during the trip.

If the wind changes direction, so too must the sail attached to the skipjack’s single mast. Hand over hand, crewmembers worked quickly to pull ropes and swing the boom in a long arc across the deck.

In the distant past, Rouse noted with a faint smile, skipjack captains would accomplish this maneuver for a more-sinister purpose. Some captains would “shanghai” a crewmember or two in Baltimore. At the end of the oyster season, those unfortunate souls would receive their “payment”: a smartly placed blow from a boom, blasting them into the Bay’s shallows.

Traditionally, skipjacks catch oysters using two mechanically operated dredges draped off either side of their hulls. The Nathan works on a smaller scale. At the appointed time, when the boat is directly above an oyster bed, the crew eases a cage-like hand scrape onto the river bottom.

Skipjack Nathan of Dorchester

The Nathan’s mainsail catches the wind near Cambridge, MD, on a quiet day. 

It bounces across the bottom at a jogger’s pace, snagging oysters and whatever else might be lurking below. Afterward, it takes four crew to lift it on deck by hand. In his experience, Macnair said, this method has brought up as many as 150 oysters. This trip’s yield was 63.

All were returned to the water. The Nathan’s state permit doesn’t allow the crew to keep what they catch. But they are careful to count the catch and report the figures to the state.

The idea for a tourism-centered skipjack in Cambridge came from a group of civic boosters known as the Committee of 100, who in 1990 proposed a handful of initiatives aimed at raising the community’s profile. At first, organizers cast about for an existing skipjack to rehabilitate. But all were either too far gone or too expensive to purchase, Rouse said.

Instead, they decided to build one from scratch. But who would build it? It had been about four decades since a working skipjack had been constructed on the Eastern Shore. The fledgling skipjack group that grew out of the Committee of 100 turned to Harold Ruark, a Shore native who had spent his life designing and building boats. His boat models could also be found in museums across the country, including the Smithsonian.

The project’s funding came from the Nathan Foundation, which was started by a prominent local family that ran a chain of furniture stores. The gift stipulated that the name “Nathan” had to appear in the vessel’s title. Although virtually all skipjacks bear female names — usually in honor of the captain’s mother — Nathan it would be for the new boat.

The number of skipjacks declined in lockstep with the deterioration of the Bay’s oyster fishery. Overfishing, disease and poor water quality conspired to eat away at the bivalve’s population year after year. From a height of nearly 17 million bushels in 1880, the annual harvest plummeted to a bottom-scraping 50,000 bushels in 2004. Last season’s harvest hit 180,000 bushels.

Still, the culture that the skipjack embodies continues to reverberate across Dorchester County. The visitors center at Sailwinds Park — another brainchild of the Committee of 100 — is topped by a sail-like structure that evokes the shape of a skipjack. The slogan of the county’s tourism campaign is “Water Moves Us.”

For its part, the Nathan is still creating moving experiences of its own. As the boat headed downwind toward the Chesapeake, Macnair turned the wheel over to the Nathan’s guests. Ananya Yarlagadda, a 13-year-old from Ashburn, VA, was one of the first to take up the offer.

She quickly got a lesson in a navigational trick as old-fashioned as the skipjack itself: dead-reckoning.

“What you do is pick your favorite tree out there and keep your eye on it,” Macnair told her.

More than a century has passed since the skipjack was the boat of choice for the Chesapeake Bay’s watermen. But on the Choptank, with the help of a steady wind and a seasoned storyteller, no other vessel will do.

Sail away on the Nathan of Dorchester... or a skipjack of your choosing

The Nathan sails out of Long Wharf, which lies at the end of Mill Street in Cambridge, MD. Public sails occur May–October. The cost is $35 for adults, $10 for ages 6–12 and free for younger ones. For information, visit or call 410-228-7141.

For public skipjack cruises at other locations, try these (fees vary):

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