Rockwell Kent was enrolled in the architecture program at Columbia University when he took painting classes at William Merritt Chases’s summer school in Shinnecock Hills, Long Island. The enjoyment he found in painting led him to transfer to the New York School of Art, where he studied under Robert Henri. In 1905, Henri introduced Kent to the summer artists' colony on  Monhegan  Island off the coast of Maine. Kent, unlike most of the artists, stayed through the winter and resided on the island for the next five years. After Monhegan, he lived for extended periods of time in  Newfoundland (1914–15),  Alaska (1918–19), Tierra del Fuego (1922–23), Ireland (1926), and  Greenland (1929; 1931–32; 1934–35).

In April of 1907 Kent had his first one-person show at the William Clausen Gallery in New York and thereafter exhibited regularly throughout his lifetime in one-person and group shows. In his landscapes, the most famous of which related to his long sojourns, Kent favored graphic designs and a precise rendering of forms with strong contrasts of light and dark. He was also renowned for the many books that he illustrated and wrote about his adventures. His considerable reputation as an illustrator was based on his striking drawings for such classics as Voltaire’s Candide and Herman Melville’s Moby Dick.