From 1906 to 1919, Glackens created more then twenty oil paintings of New York's Washington Square, as well as numerous pastels and pencil and charcoal drawings. The arist lived on the Square from 1904 to 1907 and again from 1911 to 1919. For the first four years he resided in the studio building at 3 Washington Square North. After living in an apartment on Fifth Avenue and 9th Street, he settled at 29 Washington Square West, a six-and-a-half-story apartment building called the "Washington." Glackens may have originally been drawn to the area by his close friend and colleague Everett Shinn. They both shared a major interest in picturing people making their way around the park in all seasons and weather conditions.

From 1911 to 1922, Glackens had a studio on the second floor of a three-story house at 50 Washington Square South, a few doors down from Judson Memorial Church on the southeast corner of Sullivan Street. The artist's son Ira recalled that this building was "a typical old New York house, with high ceilings, [which] had seen much better days. William had the parlor floor through. He painted in the front room, where the north light was good, and the old back parlor was used to store canvases.…There were likewise beautiful black marble mantelpieces, the last reminders of the house's stately past" (William Glackens and the Ashcan Group [New York: Crown Publishers, Inc., 195]), p. 116)

The majority of Glackens pictures of the Square are autumnal or winter scenes, not surprising since Glackens and his family regularly spent the warmer months of the year outside New York City. Glackens first developed an interest in park subjects while in Paris in the mid-1890s, and in the early years of the twentieth century painted several winter scenes featuring children skating or sledding in Central Park, and also pictured Battery Park and Carl Schurz Park in New York, as well as parks in Paris and Madrid. By the time Glackens began seriously to turn his attention to painting the Square in 1909, he had repudiated his early dark, French Realist-inspired style and had begun to master a vivid and brilliant Impressionist aesthetic.