Rebecca T. Ruark is the oldest skipjack still sailing. Built in 1886, she’s endured more than a century of hurricanes, groundings, sinkings, the Oyster Wars, dwindling oyster harvests, the decline of the fleet, and even a truck crashing on top of her while docked in Tilghman Island! Raised from the bottom of the Choptank River and restored again and again, she is more than a vessel—she’s a survivor. In 2002, the National Trust for Historic Preservation listed the fleet among America’s Eleven Most Endangered Historic Places.
And on July 31, 2003, she was officially designated a National Historic Landmark, forever securing her place in American maritime history.
Since the late 1800s, skipjacks were purpose built to dredge oysters in shallow waters using wind power alone. They were tough, low-slung, beautifully rigged—and deeply tied to the culture of the Chesapeake. The Skipjack fleet hauled not just oysters, but the dreams and fortune of working watermen. Most were named to honor the Captain’s daughter or wife. Some say this is where sailboat racing on the Bay REALLY got its start! Competition to get out to the oyster bars first, fill the decks, and get back to the dock or a buyboat to set the price for the day required a fast boat and nimble crew that knew the water and the winds.
So what led to the creation of the skipjack in the first place?
In the 1800s, oysters were thriving. With the collapse of New England beds, the Chesapeake became the oyster capital of the U.S. However, the big schooners and bugeyes used early on were too costly, too deep, and required large crews. Watermen needed something leaner. So they took inspiration from the small, two-sail bateaux used in shallow Bay tributaries. What evolved was a shallow-draft, centerboard sloop with a large mainsail and jib that a small crew could handle. Skipjacks were cheap to build and easy to operate. They had expansive working decks, low rails, and were usually around 50 feet long. And though they were sailboats, many towed pushboats—gasoline-powered yawl boats that could nudge the skipjack into position when the wind died.
By the mid-20th century, even that wasn’t enough. Oyster stocks plummeted. Regulations tightened. Powerboats took over. The skipjack fleet fell from 1,400 strong to just a few dozen. In 1985, Maryland named the skipjack its official state boat, a gesture of recognition—but not salvation. At its zenith more than 100 years ago, the Chesapeake Bay skipjack fleet numbered into the hundreds. Today only a few dozen remain and even fewer still dredge oysters. These working vessels, with long bowsprits, sweeping sails, and elegant lines are a living floating museum of Chesapeake history.
So Mark Your Calendars now for Skipjack Heritage Days!
📍 On September 13th and 14th, 2025, at Sandy Point State Park in Annapolis, a landmark event will be held celebrating these historic vessels. Held alongside the Maryland Seafood Festival, you will be able to board one of these iconic vessels while you enjoy storytelling, meet the modern day captains and crew that keep them afloat, enjoy talks on ecology and maritime history and explore the Champions of the Chesapeake family village. On Sunday there will be a parade of more than a DOZEN skipjacks at 11am and a thrilling skipjack race at noon- The first time skipjacks have raced off Annapolis in many years!
Skipjack Heritage Days isn’t just an event. It’s a movement. Chesapeake Crossroads Heritage Area and the Maryland Heritage Area Authority are thrilled to support the Skipjack Heritage Days with a grant and welcome the many partners who will be supporting the Skipjack Heritage Museum, including the Annapolis Maritime Museum, Blacks of the Chesapeake and many others who work to preserve maritime history, inspire community, and bring the skipjack back into the hearts of a new generation!
This two-day celebration will take place alongside the Maryland Seafood Festival, and with your festival ticket, you get full access to all skipjack activities—including deck tours, boat rides, storytelling, and the only skipjack race held in Annapolis. Don’t Miss Out!
And among the boats attending? Two standouts.
- Among the stars will be Rebecca T. Ruark—the oldest skipjack still sailing. For nearly 40 years, Captain Wade Murphy II sailed her out of Tilghman Island, winning more skipjack races than any other vessel, where she’s rightfully earned the nickname: The Queen of the Chesapeake.
- You can also get to know Nathan of Dorchester, and its crew! Commissioned on July 4, 1994 as the last skipjack designed to dredge under sail. Today, she serves as a floating classroom, teaching generations about watermen culture and Bay ecology.
Let’s talk about the The Queen of the Chesapeake: Rebecca T. Ruark
The Rebecca Ruark is the oldest skipjack still sailing. In fact, on July 31, 2003, she was designated a National Historic Landmark. She has survived hurricanes, groundings, and the slow decline of the fleet—thanks to the stewardship of Captains like Wade Murphy. With her long bowsprit, sweeping sails, and beautifully restored hull, she’s a living museum of Chesapeake history. And she’ll be at Sandy Point for all to admire.
She’s been called the queen of the Chesapeake, and for good reason.
Built in 1886 on Taylor’s Island by boatbuilder Moses Geohegan, the Rebecca T. Ruark is the oldest skipjack still sailing—and one of the most legendary. Originally a schooner, she was soon re-rigged into the now-iconic skipjack form: a single mast, powerful gaff rig, and low-slung deck, perfect for dredging oysters from the shallow beds of the Chesapeake Bay.
But Rebecca is more than old—she’s a survivor. She’s hauled oysters, passengers, and even oyster spat. She’s changed ports, changed hands, sunk and been raised, rebuilt again and again. In 1999, during a gale on the Choptank River, she went down in 20 feet of water. Her rescue made headlines. The state helped raise her. She was rebuilt under Coast Guard supervision, and soon, she was carrying up to 49 passengers at a time.
For nearly 40 years, Captain Wade Murphy II sailed her out of Tilghman Island. Under his helm, Rebecca won more skipjack races than any other vessel—12 victories at the Deal Island Labor Day Race alone. As one captain once said, “She can sail herself.” In 2022, disaster struck again—a pickup truck drove through a piling and landed on her deck, causing serious damage. But Rebecca was rebuilt once more. By 2023, she was back in the water, racing and dredging again—still working at nearly 140 years old.
Listed on the National Register of Historic Places and declared a National Historic Landmark, Rebecca T. Ruark isn’t just a boat. She’s a living legacy. A testament to Chesapeake craftsmanship, resilience, and pride.
Also sailing in? The Nathan of Dorchester.
Commissioned on July 4, 1994, the Nathan is believed to be the last skipjack ever built to dredge under sail. A medium-sized skipjack, she can carry about 200 bushels of oysters. Her home port is Cambridge, Maryland, and she was built to continue the tradition—not just in the water, but as a floating classroom. “Nathan” has educated thousands about skipjack construction, watermen culture, and the delicate ecosystem of the Chesapeake Bay.
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The Chesapeake Crossroads Heritage Area is a Maryland Certified Heritage Area that celebrates the history, culture, and natural beauty of Annapolis and across Anne Arundel County. A 20-plus year collaboration between Anne Arundel County, the City of Annapolis, and the Maryland Heritage Area Authority, we connect visitors and residents to over 60 incredible destinations, from world-class museums and historic homes to scenic parks, trails, nature preserves, and vibrant arts centers.
Looking for a fun way to get the family out and exploring this summer? We invite you to take part in our 2025 Historic Summer Bucket List Challenge, a fresh take on summer fun that combines learning, adventure, and memory-making. Visit our website ChesapeakeCrossroads.org, to explore a full list of attractions. Get started checking items from the Historic Summer Bucket List!