In 1988, when Cindy, my wife then, and I were living in Silver Spring, Maryland, we took the lapstrake canoe I’d built to St. Michaels to paddle the Miles River, an estuarine tributary of Chesapeake Bay. I don’t recall now why we made the 80-mile drive there—we had other places to paddle much closer to home—but the sky was clear, and the water was lightly ruffled; it was a good day to be on the water. I like to go boating with a bit of formal style, so we flew the American flag at the stern of the canoe and my family’s house flag on a short staff at the bow. The design for the flag had been passed down from my third great-grandfather Charles Cunningham and his brother, Andrew. It was the private signal flown from the highest points on their fleet of ships, barks, and brigs carrying goods across the Atlantic. In the days before radio, the signals were the first things to rise above the horizon to let merchants know whose vessel would soon be in the harbor.

Christopher Cunningham collection

There may have been something about my family’s house flag and my canoe that resonated with Judge North’s own 19th-century roots. His great-grandfather, who built ISLAND BIRD, was born in 1850, about the time the house flag was first flown by my third great-grandfather, and the lapstrake canoe I built was based on a design published by W. P. Stephens in 1889, in the same decade North’s great-grandfather was building boats.

Cindy and I paddled along the left bank of the Miles and hadn’t gone far when we rounded a blunt marshy point of land and neared a broad expanse of open land occupied by a lone, white, two-story house. A man in front of it was walking across the lawn toward us. The first thing he said was, “Is that a private signal?” It was the first, and still the only time, that anyone has recognized the flag for what it is. This was Judge John C. North, born into a family as steeped in boats as my own. When he invited us to come ashore, we pulled the canoe among the reeds and sat for a while on lawn chairs with Judge North and his wife, Ethel.

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