This painting depicts a moon rise over the Brooklyn Bridge in New York. In the foreground is the famous 120 foot schooner "Dauntless" owned by Caldwell Colt, son of the inventor of the Colt revolver. She is flying Caldwell Colt's house flag from the main mast and the New York Yacht Club flag from the foremast
Just astern of the "Dauntless" a 3- masted barque has just been towed from its berth and a schooner is about to pass the barque on it's starboard side.

"Dauntless" was designed by J.B. Van Deusen of Noank Connecticut and built in 1865-66 at the Forsyth and Morgan shipyard, Mystic Bridge Connecticut for S. Dexter Bradford, Jr., who named her "L'Hirondelle". She was bought by James Gordon Bennett Jr., in 1867, who added 23 feet to her length and renamed her "Dauntless". He raced her for 11 years. He also became the Commodore of the New York Yacht Club. In 1879 she was sold to John R. Waller who owned her for 3 years before Caldwell Colt bought her in 1882. "Dauntless" remained in the Colt family for 33 years, until the end of her days.

Her racing fame derives largely from the two exciting transatlantic match races she sailed- westbound under Bennett's flag in 1870 against the "Cambria", which she lost by only 1 hour and 43 minutes and the 1887 race eastbound against "Coronet", under Colt's flag, that she lost by 30 hours. However on one day of that race, on March 25, "Dauntless" logged 328 miles from noon to noon, a record that stood until broken by the much larger "Atlantic" with a 340 mile record in 1905. In both races "Dauntless" was skippered by the famous Samuel "Bully" Samuels, a former clipper ship skipper.

"Dauntless" also raced in the 1870 America's Cup, where 14 American schooners raced the "Cambria", from England. "Dauntless" finished 5th, behind "America" who finished 4th. The race was won by "Magic" and "Cambria" finished 10th.