It is believed to follow the course of an old Indian trail that became an important road in the 17th century between the Dutch settlement of New Amsterdam and the British New England Colonies.
The road became a street when row housing was being built in Harlem during its rapid urban expansion following the end of the American Civil War.
Its 17th-century origin as part of the Eastern Post Road accounts for its non-conformance to the grid pattern proposed by the Commissioners' Plan of 1811.
[3] On September 30, 1956, an American pilot named Thomas Fitzpatrick landed a stolen plane near 191st Street in front of a New York City bar where earlier he had been drinking and made an intoxicated barroom bet that he could travel from New Jersey to New York City in 15 minutes.
[4][5] In 2000, Mayor Rudolph Giuliani signed a bill adding the name "Juan Pablo Duarte Boulevard" to St. Nicholas Avenue for the stretch from Amsterdam Avenue and West 162nd Street to the intersection of West 193rd Street and Fort George Hill.