After a brief period of depression and drinking as part of an apparent mid-life crisis, the forty-five-year-old Hassam then committed himself to a healthier life style, including swimming. During this time he felt a spiritual and artistic rejuvenation and he painted some Neo-Classical subjects, including nudes in outdoor settings. His urban subjects began to diminish and he confessed that he was tiring of city life, as bustling subways, elevated trains, and motor buses supplanted the graciousness of the horse-drawn scenes which he so enjoyed capturing in earlier times. The architecture of the city changed as well. Stately mansions gave way to skyscrapers, which he admitted had their own artistic appeal: "One must grant of course that if taken individually a skyscraper is not much of a marvel of art as a wildly formed architectural freak. It is when taken in groups with their zig zag outlines towering against the sky and melting tenderly into the distance that the skyscrapers are truly beautiful." Hassam's urban paintings took on a higher perspective and humans shrank in size accordingly, as illustrated in "Lower Manhattan" (1907). He began to spend only his winters in New York and traveled the balance of the year, calling himself "the Marco Polo of the painters." In 1904 and 1908, he traveled to Oregon and was stimulated by new subjects and diverse views, frequently working out-of-doors with friend, lawyer and amateur painter Colonel C. E. S. Wood. He produced over 100 paintings, pastels, and watercolors of the High Desert, the rugged coast, the Cascades, scenes of Portland, and even nudes in idealized landscapes (a series of bathers comparable to those of Symbolist Pierre Puvis de Chavannes). As usual, he adapted his style and colors to the subject at hand and the mood of place, but always in the Impressionist vein.