Jack Sherwood was a character who loved to write about characters — watermen, boatyard workers, vagabond cruisers and others he encountered on and around Chesapeake Bay.
A onetime feature writer and columnist for the Washington Star, Sherwood crafted the monthly Bay Tripper column for Soundings for nearly 20 years. His last piece, in the September 2014 issue, was about a cherished summer outing with his granddaughter Claire aboard his beloved Sparkman & Stephens-designed Sailmaster 22, Erewhon. Sherwood died Dec. 7 in Maryland of cancer at the age of 84.
Former Soundings editor-in-chief Bill Sisson says Sherwood was a “sailor’s sailor and a writer’s writer. Jack was an original. With his strong reporter instincts and a good ear, he was constantly finding colorful waterfront characters to write about.”
Sisson fondly recalls Sherwood’s columns about Capt. Freddy, the homeless sailing veteran of the Florida Keys, and those about a former Washington, D.C., lawyer and liveaboard who kept popping up at anchorages in his junk boats until he (and his junks) finally disappeared.
“He loved sailing, and he loved the people he met along the way,” Sisson says. “In the process he became as much of a character as the people he wrote about — a lovable curmudgeon who called things like he saw them, with an aversion for yachting pretensions and people who took themselves too seriously.”
John Barry, a retired Caribbean schooner captain and close friend of Sherwood’s, met the writer decades ago through his wife, Betty, who was an administrative assistant at the Bay Yacht Agency in Eastport, Maryland. Sherwood wrote about Barry’s daysail operation, Sail Daily Aboard Lady (with a new Ericson 35), in the summer of 1980 in the Washington Post’s Weekend section after leaving the Star. “That piece made my season,” Barry says. “I had to turn away guests and hire someone to answer the phone. This was the beginning of a lasting friendship.”
Barry says he hugely enjoyed the company of Sherwood and his wife. “I have never met any two people with as much flair and fun,” he says. “It was always an adventure when sailing with them. Our personal favorites were cruising Nantucket and Martha’s Vineyard out of Newport, and Bluejacket, an Alden 54, in the Grenadines. The stories are never-ending.”
Barry admired Sherwood for many things, but none so much as his obsessiveness while working on Erewhon “in the most frightful conditions,” he says. “I remember too well 38-degree, gray overcast days working off Spa Creek on his beloved,” Barry says. “I was fascinated with his to-do list. He told me once that he loved to mark off finished projects, which gave him a sense of accomplishment.”
When Sherwood was diagnosed with cancer last summer, he entrusted Barry with selling Erewhon. “It was bittersweet,” Barry says. “To me, Erewhon was a good friend and part of Jack’s family.”
Another of Sherwood’s friends, Winston Groom, a Southern novelist and nonfiction writer and the author of Forrest Gump, bought the boat. He sails it in Mobile Bay, Alabama. Groom and Sherwood were reporters together at the Star.
In a remembrance in the Annapolis Capital Gazette newspaper, Groom writes, “With a Runyonesque flair, [Sherwood] brought alive the likes of ferry-boat operators, tea-room waitresses, pigeon racers, Linotype workers, toll-booth trolls, tugboat drivers and hundreds more of such ilk, who likely never dreamed they were important enough to decorate the pages of a big-city newspaper or a magazine — as well as individuals with delusions of grandeur. Better yet, he made the reader understand their importance, too.
“Sherwood’s great gift was the ability to discern hidden, intriguing facets from the hoity-toity to the hoi polloi,” Groom adds. “He could make them talk about themselves, often by asking innocently outrageous questions. Take Tony, an 81-year-old Italian bread baker in Baltimore’s Little Italy, who spurned retail customers wanting to buy a loaf from the bake shop below his dingy row house apartment, which his father, ‘Poppy-pop,’ had started in 1914. Sherwood asked him about retirement.
“We sell 1,000 loaves a day, that’s enough,” Tony replied furiously. “We could bake and sell 5,000 loaves a day if I expanded, but what for? I don’t wanna be a millionaire. I ain’t married. I ain’t got children. I want to stay here until I die. Poppy-pop liked it here. I like it here.”
(The reference to Tony the baker is from Sherwood’s 1994 book Maryland’s Vanishing Lives, which profiled people whose jobs were disappearing.)
Sherwood’s last column was in the October 2016 issue of Spinsheet, the Chesapeake Bay sailing magazine. He spoke of “an unfortunate illness” that had persuaded him to sell Erewhon and retire from solo sailing. “My demanding, intimate and all-consuming relationship with a classic Sailmaster/C sloop built in Holland has run its course after 30 years of cruising the middle Chesapeake Bay and its environs,” he wrote.
Reminiscing, Sherwood said he found Erewhon after he was inspired by Robert de Gast’s classic account of his solo Sailmaster cruise of the Delmarva Peninsula in the book Western Wind, Eastern Shore. “Our typical daysailing course in a southerly was a close starboard reach over to Kent Island, tacking over toward Thomas Point Light and beyond, with a broad starboard reach back to Kent Island, followed by a gybe and a reaching run homeward,” Sherwood said. “Boring? Hell, no. I always focused on performance and never tired of this routine.”
Over time, Sherwood tricked out Erewhon for single-handing — he preferred to sail alone — with innovative ideas and solutions. “The boat never failed me in three decades,” he said.
This article originally appeared in the March 2017 issue.
