Trans-ocean racing is still a relatively new sport, but was simply unheard of in the 19th century. A lively dinner discussion at New York’s Union Club in October 1866 resulted in the first Trans-Atlantic challenge. The contenders: Pierre Lorillard’s Vesta, George and Franklin Osgood’s Fleetwing and New York Herald founder’s son, James Gordon Bennett Jr.’s Henrietta—all two-masted schooners. It was a winner-take-all —$30,000 plus bragging rights. On the morning of December 16, the starting gun was sounded and the vessels weighed anchor in the New York Narrows. Next stop—Cowes, England. Demers’ evocative painting depicts the end of the first day, the vessels having logged nearly 300 miles and still in sight of each other. By day two Fleetwing had a twenty-mile lead on Henrietta and a forty-mile lead on Vesta. The racing was serious. Remarkably, after 3,000 miles of intense sailing all three yachts finished within hours of each other. On December 26 at 3:46pm Henrietta was first, followed by Fleetwing at 1:00am and the ill fated Vesta, whose local English pilot had taken them in the wrong direction, allowing Fleetwing to pass her nearly in sight of the finish. Demers’ extraordinary painting transports us hundreds of miles to sea to experience the majesty of these three great vessels underway as if we were sailing alongside them.