"One can't paint New York as it is, but rather as it is felt." (O'Keeffe in Peters, p. 277) In 1925 O'Keeffe and her husband Alfred Stieglitz moved into the top floor apartment of the Shelton Hotel, where each was inspired to depict views of Manhattan. Between 1925 and 1926 O'Keeffe painted her well-known skyscraper series: among these are City Night 1926 (Minneapolis Institute of Arts), The Shelton with Sunspots 1926 (The Art Institute of Chicago), New York, Night 1929 (Nebraska Art Association), and Radiator Building--Night, New York 1927 (Alfred Stieglitz Collection, Carl van Vechten Gallery of Fine Arts at Fisk University). She then turned to the East River pictures in 1928.

In a letter dated January 10, 1927 to the writer Waldo Frank O'Keeffe remarked, "The light on the river is very bright this morning." (in Cowart and Hamilton, p. 184) This light inspired the artist to paint five known views of the East River. The present picture, a pastel, is strikingly similar to her first oil of this subject East River, New York, No. I, 1926 (Wichita Art Museum). At this time, Stieglitz was also capturing expansive views of the city: From the 30th Story, Shelton Hotel, Looking East, a gelatin silver print from 1927 (National Gallery of Art) shows an almost identical scene. In his review of O'Keeffe's pictures from the 1920s, Waldo writes, "How could you expect New York to admit that what it likes in O'Keeffe is precisely the fact that she is clear as water?" (in Cowart and Hamilton, p. 281)

Although O'Keeffe struggled emotionally and often felt constrained in New York (she would leave for the Southwest one year later), her pictures from the twenties reflect an artist with clear focus and confidence. It is interesting, as Roxana Robinson notes, "The winter of 1927-28 marked a general decline in the art market. For O'Keeffe, however, it was a banner year: it marked the highest price ever brought by O'Keeffe, by a woman artist, or by a living American artist."(R. Robinson, Georgia O'Keeffe, New York, 1989, p. 304)