When commercial oystering was at its peak in the late 19th and early 20th centuries, an estimated 2,000 skipjacks plied the Chesapeake Bay. The successor to the larger schooner-style bugeye, these wooden sailing vessels were specifically designed for dredging oysters from the Bay’s shallower waters. Today, only about 40 skipjacks remain, fewer than half of which still dredge. These boats comprise the last commercial sailing-powered fishing fleet in North America. In this painting, titled The Kathryn off Thomas Point Lighthouse, maritime artist John Barber depicts one of the few historic skipjacks still in service today.
Built in 1901 in Crisfield, Maryland, by James E. “Jimmy” Daugherty, Kathryn is one of the fastest skipjacks on the Bay. She is distinctive for being one of the few skipjacks planked fore and aft with a rounded chine—most skipjacks were cross-planked with a hard chine). She measures 50 feet long with a 16-foot, 8-inch beam and 4-foot, 2-inch draft.
In 1994, Kathryn was designated a National Historic Landmark, one of only three skipjacks to receive such a distinction. Excellent maintenance over the years and a three-year reconstruction project that started in 2013 have kept her in working condition for more than a century. Today, Kathryn is privately owned and sails out of Deal Island. She is one of the oldest skipjacks in the Bay’s fleet.
Barber, who lives in Richmond, Virginia, has spent more than four decades chronicling the Chesapeake Bay’s maritime history. Drawn to the subject since childhood, Barber decided on this career path at age 7, after witnessing an artist painting a lighthouse near Cape Hatteras, North Carolina. “I remember feeling as if it were magic that he was using these bits and dabs of oil paint to create this magnificent illusion,” Barber recalls.
Barber earned his BFA from Virginia Commonwealth University in 1969 and has spent most of his career focused on the Chesapeake. “I chose that as a subject because I wanted to be a specialist as opposed to a generalist,” he says. “That way, I figured I could get to know the subject intimately.”
Barber has owned 17 boats and spent time sailing with many clients. One of his most memorable excursions involved sailing from Annapolis to Martha’s Vineyard aboard Walter Cronkite’s yawl Wyntje in order to paint the vessel entering Edgartown Harbor. Barber is a Fellow Emeritus of the American Society of Marine Artists. In 2009, he received the Distinguished Service Award by the National Maritime Historical Society.
May 2025
