Born in St. John's, Newfoundland, Maurice Brazil Prendergast moved to Boston with his family in 1861. By his early twenties, the young man was apprenticed to a card painter, to which he attributed his life-long interest in flat, boldly-colored patterns. In 1891, Prendergast traveled to Paris, where he studied and painted for the next four years. His Parisian watercolors focus on the city's cosmopolitan splendors and invoke the fêtes champêtres of Watteau and the idylls in French parks by Edouard Manet, Claude Monet, and Pierre-Auguste Renoir.

Unlike these artists, however, Prendergast's technique assimilated the latest advances by Post-Impressionists including Paul Gauguin, Edouard Vuillard and the Nabis. This second group of artists revolted against fidelity to nature by permitting artistic expression to dominate subject matter, and their innovations liberated Prendergast from a strictly representational approach in his work. He would replace nature with his own imagination, painting whimsical patterns in bold colors to create charming and sophisticated views of leisure – the parade of strollers in the park, the bustle of shoppers along the streets, and the holiday atmosphere of summer outings at the beach.

During the next twenty years, Prendergast spent time in Boston, Venice and Paris, where he continued to develop his painting technique. During the late 1890s, he began exhibiting at the New York Watercolor Club and by 1900, had his first one-man show at Macbeth Gallery. In 1908, he participated in the exhibition of The Eight, also at Macbeth, and several years later, exhibited seven paintings in the pivotal 1913 Armory Show.