At 1pm on 11th December 1866, three schooners sailed from Sandy Hook, Connecticut, their destination was the Needles, near Cowes in the Isle of Wight. The three yachts taking part in ‘The Great Atlantic Yacht Race’ were the Henrietta, owned by New York Herald publisher James Gordon Bennett, Jr., George A. Osgood’s Fleetwing, and the Vesta, owned by the tobacco manufacturer, Pierre Lorillard. Each owner wagered $30,000 on what was the first ever trans-oceanic yacht race, and while Osgood and Lorillard remained in New York, Bennett set sail with his crew.

A flotilla of sailing craft escorted the three yachts from New York to the docks at Sandy Hook, which were lined with a cheering throng. One day into the race, the Henrietta opened a lead on the other two craft and later the Vesta, under the command of Captain Dayton, parted company with the Fleetwing commanded by Captain Thomas. The trailing yacht ran into trouble on the eighth day of the race when she encountered a heavy gale that caused six men to be washed overboard, all of whom were lost along with the yacht’s jibboom.

The Henrietta won the race and the $90,000 prize (more than $2 million in today’s money), taking 13 days, 21 hours and 55 minutes to complete the crossing. In spite of her earlier tragedy, the Fleetwing came second due to a navigational mistake by the pilot who joined the crew to guide them safely to their goal. Due to misty conditions, he mistook the lighthouse at St. Katherine for the one at the Needles.