Long before the Macy's arrived, Herald Square was home to the headquarters of namesake New York Herald newspaper.
In this vintage photograph captured around 1901 by the Detroit Publishing Company you can see the Herald Building front and center along with well-dressed pedestrians, horse carriages and merchants. On the right you can see the tracks of the Sixth Avenue Elevated.
Here is a Google Streetview of approximately the same view today. Check out the specimen page in the Library of Congress Digital Archives for more info on the photo.
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