At the age of 29, Tom Day took over a magazine focused on canoes and moved it from upstate New York to New York City and renamed the magazine, The Rudder. Among his many accomplishments, he created the first yacht race to Bermuda in 1906. The race started off Brooklyn, N.Y. with a fleet of three small boats. At the time reaching Bermuda was considered a dangerous endeavor. In fact, one of the three boats, Lila broke her mast 90 minutes after the start and was towed back to Brooklyn, by Tom Day.

Day’s concept was that small yachts could sail offshore. It was controversial at the time. Adding to the narrative, a woman 20-year-old Thora Lund Robinson, was on the crew list of one of the racing boats, Gauntlet. Day’s goal was to demonstrate that going to sea should be available to everyone. Day convinced the skeptical race committee that Thora should be able to join her husband of six weeks, George Robinson, for the race. When Gauntlet crossed the finish line off St. David’s Lighthouse, Thora was at the helm and waved an American flag. Day’s concept was vindicated. Day was the sailing master of Tamerlaine the first boat to the finish line in Bermuda that year.

Tom Day’s publication gained stature in New York. He spoke out on issues that he believed needed addressing. His goal was to encourage all people to participate in sports not just read about them. Day was also a champion of amateur competitors. He described the crew roster of Tamerlaine as, “A telegrapher, an artist, an artisan, a gentleman of leisure, a schoolboy, and an editor.”

John Rousmaniere in his book, A Berth to Bermuda, Mystic Seaport and The Cruising Club of America, 2006, reports that Day sometimes have a scolding pen when he wrote. Here is an example of one editorial, “I am sick of hearing that we are a lot of shore-skulkers. Central Park sailors; that we can build racing machines and win with them, we have neither the craft nor the skill and pluck to sail on deep water, or even go out of the sight of land.” Thomas Fleming Day proved them wrong. Sailors have been racing and cruising on blue waters ever since.

— Gary Jobson