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Bon voyage but not goodbye, Bay Tripper

Jack Sherwood possesses one of the most authentic voices in marine publishing over the last two decades.

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For the last 17 years, Jack wrote a monthly column for Soundings called “Bay Tripper,” in which he chronicled the various characters and places he encountered as he worked his way around Chesapeake Bay on his beloved 22-foot Erewhon, a Sparkman & Stephens-designed Sailmaster.

The column has ended, but Jack will continue to write an occasional story for Soundings. He’s got his teeth into a good one at the moment, which you’ll read in a month or two.

I want this column to be our thanks to the Bay Tripper for nearly 20 years of sea stories.

I always felt that Jack didn’t write so much about boaters as he did characters, the offbeat waterfront types who give our world color and texture. Those were among the stories I remember best.

He found value in their dreams and work, and through his skill as a storyteller, he gave their lives and stories dignity. Waterman, boatyard worker, vagabond cruiser, a poor soul battling the tides of life to resurrect a boat found moldering in some bone yard on the Bay … we pulled for these threadbare dreamers and their projects, even when we knew they were, in all likelihood, going to fall short — but never fail. Not by Jack’s measure or ours.

It’s not really surprising that Jack, over time, became as unique and idiosyncratic as the people he covered. He’s authentic, a fixture on the Bay, be it sailing through a crowded mooring field or swinging on the hook in a quiet creek with a good cigar and a couple of fingers of something medicinal swirling in a glass.

He remains an endearing curmudgeon, a frugal, plainspoken sailor who calls things as he sees them and doesn’t believe in sugar coatings. I’ve gotten my share of feisty missives from Jack over the years. I hope to get a few more.

Jack started in newspapers in 1960 and spent nearly 20 years at The Washington Star as a columnist and feature writer. At his core, Jack remains true to his roots as a good, old-fashioned newspaperman in the best sense of that phrase. He is a skilled reporter with good instincts and a great ear — a very good writer who is fair and accurate. His 1994 book Maryland’s Vanishing Lives is wonderful.

And he never saw the job of his column as puffing up people or shilling for products. He preferred pricking stuffed shirts.

He has had a long and loving relationship with his lovely sailboat, which he bought in 1985. “Erewhon has been my companion and partner for 28 years. My late wife called it ‘that stupid boat,’ ” he says. “Even today, I visit with her almost every day and day-sail at least four times a week in-season, although I no longer sail her in winter. Erewhon has also taught me how to do many things, among them painting, sanding, varnishing, and rigging for single-handing, which I prefer.”

Jack’s column spoke to anyone who loved simple, unpretentious small boats. When he attended sailboat shows, he rarely went aboard the large boats. “Instead,” he says, “I preferred those usually under 30 feet, searching for clever ideas I could confiscate. I enjoyed prowling the tents as much as anything, but I really got sick of the professional Navy-blue blazer set selling Rolls-Royces.”

And he wasn’t above laughing at himself and the blunders, mistakes and “close shaves” that befell him over nearly 50 years on the Bay. They included “one shipwreck, one dismasting, a few nasty storms, once falling overboard and a near collision with a tugboat pushing a huge barge.”

Although he had an appreciation for small, traditional powerboats, Jack, who claims to be 79 (wink, wink), never made the journey to the so-called dark side. He had trouble imagining it.

“No sheets/halyards to winch, pull, adjust, trim and make fast?” he asks. “And what of fuel expenses? I am a cheapskate rag-hauler! Just turn a key and watch the boat take care of itself? No watching for wind shifts from the masthead vane or on sail telltales? No tacking into the Annapolis harbor alone, showing off under full sail while startling fellow boaters in the tight mooring field?”

No, Jack, not you. May you and Erewhon NEVER go quietly into the night.

“In little boats such thoughts are possible and the dreams of ordinary men can become realities. In little vessels there is joy. In larger vessels there is travail and perplexity.”

— Ernest K. Gann

November 2014 issue