Hassam began his career as an engraver and printmaker in Boston. He supported himself by designing book illustrations while painting on the side. In 1883, Hassam exhibited a watercolor at the National Academy of Design, and it was in that year that he began to identify himself as an artist. Hassam sailed for Paris in the fall of 1886. His work was accepted into the 1887 Salon.
Hassam returned to the United States in 1889 and settled in New York. He traveled during the summers in New England, and painted both scenes of urban life and more bucolic images of the seaside and gardens. Within a few years, he was a fixture of the annual exhibitions at the American Water Color Society, the National Academy of Design, and others.
Hassam’s career blossomed over the next years, as he exhibited throughout the United States and traveled regularly to Europe. Hassam sold his first painting to a museum in 1899 and by 1911 he was in the collections of most major American museums.