In 1971 the United States Postal Service issued an eight-cent stamp to mark the centennial of the artist John Sloan’s birth. Designed by Bradbury Thompson and Robert J. Jones, the stamp features a reproduction of Sloan’s 1907 painting Wake of the Ferry II. The ferry passenger’s mobility—pictured in the midst of a journey—recalls the transport of items sent through the mail. The stamped letter, when in a state of transit between points of departure and destination, is unconnected to place. Sloan worked as a newspaper illustrator in Philadelphia before moving to New York City in 1904, and his approach to painting retained some of the visual elements and narrative strategies that he developed in this line of work. Further examination of the role urban transportation plays in the artist’s oeuvre expands the understanding of Sloan’s long engagement with locomotion as both subject matter and stimulus for his work.