In 1923 Marguerite Zorach and her husband, sculptor William Zorach, purchased a house on Georgetown Island in Maine, that became their summer residence. During the late 1920s, she was influenced by the recent vogue for folk painting and regionalism and began to paint scenes of everyday life in rural Maine. Christmas Mail represents a mail delivery made by a horse-drawn sled to Todd's Groceries in Georgetown, a store that also served as the town's post office. The Zorachs shopped at Todd’s, and a number of figures in the painting can be identified as local residents.

Early in 1937, the Section of Fine Arts, Public Buildings Administration, of the Federal Works Agency invited Zorach to submit a design for a mural to decorate the lobby of the newly constructed post office in Peterborough, New Hampshire. She used a slightly modified version of Christmas Mail for this new undertaking and at some point in the process redated the painting 1936. The design was accepted, and the mural was installed on November 14, 1937. Despite the mural’s New Hampshire locale, Zorach persisted in inscribing the store’s door lintel with the name of the Georgetown, Maine, post office and store.