John SwainJay Fleming

In the mid-1960s, John Swain apprenticed at Applegarth’s Boatyard in Oxford on Maryland’s Eastern Shore and has specialized in Chesapeake Bay watercraft ever since. Today, he has his own shop near Chestertown.

At 7:30 on a September morning, boatbuilder John Swain takes a break from projects at his boatshop to show me his world. He often starts such visits on the wharf at the foot of Cannon Street in the historic colonial port of Chestertown, Maryland, on the Eastern Shore of Chesapeake Bay. On this day, a sultry wind is blowing down the Chester River when Swain and I arrive at the Chestertown waterfront. Sometimes Swain is a bit paternalistic about the classic watercraft tied up at the wharf here. To be sure. This is not his job; there’s a crew of professional sailors and custodians to tend to the boats. But Swain has built or rebuilt them all. They are a bit like his children—never fully out of mind.

learn from the masters

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