This work is straight from the heart of the 19th century and the era of clippers, whalers and the first pleasure yachts. Two schooners race upon a hearty north Atlantic swell, gamely calculating their unmarked ocean intersection with the large square-rigged merchant ships sailing with the wind off starboard. The conditions are trademark Buttersworth, with a strong bright break in the cloudy, deep sky. The quick tacking of the schooners should keep them clear of the well-defined larger ships.

The shadow placement along the sails and the striking yet harmonious colors throughout the work show some of the drama Buttersworth would apply to accentuate a viewer's senses. The sharp details and gracefully drawn hull lines of the schooner yachts well represent possibly no more than a handful of yachts in the late 1850s. They are definitely of the larger ‘New York' keel schooners rather than the centerboard schooners of the Boston area, necessitated by shallower waters. Only a few names are recorded for this era: NORMA, FAVORITE, HAZE, VOLANTE and the aptly named MYSTERY, among others.

Informal speed trials soon led to set matches for stakes, and the organization of formal yacht clubs. Five such New York area clubs were in existence prior to the disruption caused by the Civil War. HARLEM, HOBOKEN, BROOKLYN, JERSEY CITY and BUFFALO rose alongside the N.Y.Y.C. from 1856 to 1860. The 1860 roll of the N.Y.Y.C lists 21 schooners belonging to the prestigious organization's members. Here two of their earliest match skills and challenge the ocean.