He moved to New York City in 1858 and established a new store named "R.H Macy Dry Goods" at Sixth Avenue on the corner of 14th Street.

[10] The store later moved to 18th Street and Broadway, on the "Ladies' Mile", the elite shopping district of the time, where it remained for nearly forty years.

In 1875, Macy took on two partners, Robert M. Valentine (1850–1879), a nephew; and Abiel T. La Forge (1842–1878) of Wisconsin, who was the husband of a cousin.

The renovations completed in November 2015 but Macy's continues to modify the store to suit changing customer tastes and maximize return on the real estate.

[25][26] In August 2014, Macy's agreed to a $650,000 penalty proposed by the New York Attorney General to settle a number of claims of racial profiling and false detention involving nearly two dozen African-American, Latino and other customers at the Herald Square store who had lodged complaints in February 2013.

As part of the deal, the retail group agreed to introduce policies to ensure all customers were treated equally regardless of race or ethnicity.

[30] Macy's is noted for its elaborate animated holiday and Christmas window displays in many of its U.S. stores, but most notably at the Herald Square location.

In summer 2007, Macy's mounted a public art exhibition at the Herald Square flagship, using its windows to display pieces from fashion designers Misaki Kawai, Anna Sui, and John F. Simon Jr. Art Under Glass was viewable to the public through that year's fashion week.

[34] Other events include: Through a partnership with tech retailer b8ta, "The Market @ Macy's" section features pop-up spaces for new brands.