The four masted bark SHENANDOAH is shown in profile from the port bow as she works to weather through heavy seas with the sun breaking through the late afternoon clouds. The ship is on starboard tack under courses, upper and lower topsails & lower top gallants. The fore and main upper top gallants are shown luffing in their clewlines and a trysail has been set on the jigger in place of the usual spanker. The gaff topsail is furled on the mast and the vessel is not carrying a jib boom, all four headsails are tacked to the bowsprit. The composition suggests that SHENANDOAH is either preparing for or has just passed through some inclement weather.

When launched in November, 1890, SHENANDOAH was the largest sailing ship in terms of cargo carrying capacity built in the United States up to that time. Carrying 33,000 square feet of sail, she was also extremely fast. For most of her career she was employed in the Cape Horn Trade to San Francisco carrying general cargo and later bulk cargoes of wheat and coal. She also made several passages to Australia, France and England. In July, 1907 she was laid up in San Francisco until February, 1910 when she made her last passage around Cape Horn with a cargo of asphalt, lumber and scrap iron salvaged from the San Francisco earthquake and fire of 1906. SHENANDOAH's long and successful career was ended off the beaches of Fire Island when she was rammed by the steamship POWHATTAN and sank. Her wreck was blown up by the U.S.Coast Guard in March, 1916.