Representing the most favored subject matter of J.E. Buttersworth, yachts racing, this painting offers an important view of the start of the world’s first transatlantic yacht race held in 1866 as the schooners head out past the sandy hook lightship. In his book, "J.E. Buttersworth, 19th Century Marine Painter", biographer, R.J. Schaefer has noted six views by the artist of this event.

Identificaton of the vessels is by the special colored flags worn by the yachts. Blue for HENRIETTA, owned by James Gordon Bennett, white for VESTA, owned by Pierre Lorillard, and red identifying George and Franklin Osgood’s famous FLEETWING. $30,000 was put up by each owner on a bet. Bennett’s HENRIETTA was the first to finish off the Isle of Wight with a time of 13 days, 21 hours and 45 minutes winning the unheard of purse for 1866 of $90,000.

Buttersworth’s attention to minute detail shows the racing crews lining the windward rail on all three yachts with all sails set on a broad reach. The elongated hulls and colorful treatment of sea and sky make this an excellent example of the Buttersworth style.