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Racing small boats over long courses had its inception over one hundred years ago. The late Thomas Fleming Day, then editor of The Rudder, caused consternation in the ranks of yachtsmen and laymen alike when, in 1904, he proposed to hold an ocean race for small yachts from New York to Marblehead, Mass, a distance of 330 miles. This race was for boats with waterline length of less than 30 feet. Many in the press and public in general called him foolish; others downright crazy. But, despite these dire prophecies of danger, he persisted. He knew that small crafts, if properly designed, built, and handled, were just as safe at sea as large ones. So he preached, prayed, cajoled, and cussed a bit; organized his race; and ran it to a successful conclusion., without damage or loss of a boat, or harm to any individual.
Rhode Island Yacht Club members of great fortitude, Charles F. Tillinghast and Dwight B. Hill, entered this first small yacht challenge race. Tillinghast, a descendant of Stephen Hopkins, signer of the Declaration of Independence, engaged the Fall River Shipyard to build a yacht that could withstand the conditions expected to be encountered in an ocean race. George Owen (1877-1959), an 1894 graduate of MIT, was employed as a designer at the Shipyard at that time, having previously worked in the drafting department with Herreshoff Manufacturing Co. from 1898-1901. Owen designed the Little Rhody to meet the criteria of Thomas Day’s race, with an overall length of 34 feet seven inches and a waterline length of 22 feet. It was likely the smallest boat in the race. Nine stalwart skippers entered the race, with six completing the task within the time limit.
Sir Thomas Lipton, renowned tea baron and four-time contender for the America’s Cup, was a sports patron and approved of Day’s concept for a small craft ocean race. He provided the 100-guinea Lipton Cup that would be presented to the winner.
The race began on July 2, 1904, from Gravesend Bay in New York by way of the Nantucket Lightship to Marblehead, Mass. This race was sponsored by the Brooklyn Yacht Club. The New York Times reported that the sloop Little Rhody, owned and sailed by Charles F. Tillinghast of the Rhode Island Yacht Club, captured the Lipton Cup in the Brooklyn Yacht Club’s ocean race, finishing at 9:38 on Monday night, July 5, 1904. The Little Rhody had completed the race in 58 hours and 38 minutes. The sloop Newasi from the Larchmont Yacht Club, with skipper A.H.W. Johnson, was the second boat to finish, winning a $200.00 marine painting for second place. Third place was taken by skipper Gilbert R. Hawes of the Brooklyn Yacht Club, aboard the Ray II, winning a $75 Chelsea ship’s clock. Others finishing the race were: the yawl Fenshaw, skippered by F. Maier from the New Rochelle Yacht Club; the sloop Mignon, skippered by Dr. Joseph Fournier from the Indian Harbor Yacht Club; and the sloop Eumarrier, skippered by Dwight B. Hill from the Rhode Island Yacht Club. The cutter Mopsa, skippered by F. C. Sullivan of the Harlem Yacht Club, withdrew from the race and put into Vineyard Haven. The yawl Sea Bird, skippered by Thomas F. Day of the Springfield Yacht Club, came in nearly twenty-three hours behind her time-allowance limit. So far as known, the only mishap, besides the disabling of The Siren, occurred to the Ray II. One of her crew, George W. Robinson, fell overboard on Sunday near Nantucket Lightship. He was quickly rescued.
And so, from that day, ocean racing became an accepted branch of the sport of yachting, to enjoy varying prosperity up to the present time. Thomas F. Day’s next undertaking was to organize and promote a race for small boats to Bermuda. This race took place in June of 1906, covering 650 miles of open ocean. It was considered dangerous and foolhardy, crossing the notorious Gulf Stream , with the possibility of half the fleet smashed by the tail end of a West Indian hurricane. He ran the race anyway, again without accident, thus putting ocean racing on a firm footing from which it has never slipped. The Bermuda races today are huge sailing events, but it must be remembered that Tillinghast, Owen, and Day were the first to answer the challenge.
Charles Tillinghast continued successful ocean racing aboard Little Rhody, winning the Bristol Yacht Club’s ocean race in 1905. Two years later, on July 1, 1907, the New York Times’ headline read: “Little Rhody’s Crew Washed Overboard, but Finished First.” Sudden squalls and heavy seas made the ocean race of the Bristol Yacht Club from Bristol to Montauk Point an intensely thrilling contest. The race covered a distance of 88 nautical miles. Tillinghast and his nephew, James S. Tillinghast, aboard the Little Rhody, were swept overboard when off Brenton’s Reef by a sudden squall which almost capsized their craft. They were saved by their comrades, and undaunted by their mishap, they drove the Little Rhody through the high seas and brought her home a winner.
George Owen continued designing yachts, producing over 200 designs for yachts and commercial vessels, including the Mayflower II. He also became a professor of naval architecture and marine engineering at his alma mater, MIT, from 1915-1941. One of his students at MIT was Phillip Rhodes, who went on to become a renowned designer in his own right.
Charles Tillinghast’s winning Lipton Cup for the first ocean race for small yachts, won in the race that Thomas Day instituted in 1904, now resides at the Rhode Island Yacht Club, his affiliated club at the time of his victory. It was generously donated by the Tillinghast family in 1996 and now is the centerpiece of the Club’s trophy collection.