In the 1870s and 80s, the Herald Square neighborhood was part of New York's Tenderloin District, filled with dance halls, cafes, and bordellos. Reformers tried to clean up the area in the 1890s and newspapers - including the New York Herald, which gave the area its name - established offices there briefly. Macy's moved to the neighborhood in 1902, followed by Saks and Gimbels, and Herald Square replaced the Ladies Mile of lower Broadway as the city's major department store distrect.
The Herald Square clock can be seen at the edge of the painting. Every hour, two bronze figures pretend to strike the bell as Minerva and her owl look on from above.
The Macy's Thanksgiving Day Parade began in 1924 as "Macy's Christmas Parade," and the giant balloons made their first appearance inc 1927. The parade has since become an annual New York tradition. Michael Scacco, carrying the sign in the middle of the painting, and Steven Krauss, in the red jacket, both worked for Macy's and were involved with parade preparations.