5. Pete’s Tavern (1864)
Pete’s, also known as “the tavern that O. Henry made famous,” is a vestige of the Civil War era. The building itself dates back to 1829, though it was not operated as a bar until 1864. Its large signs claiming to be the oldest bar in the city have been greatly disputed by McSorley’s.
As was the case for most of the previous pubs, Prohibition meant business as usual, though its brief status as a flower shop was one of the more creative covers. It lies in the Gramercy Park Historical District, and though it has not been specifically designated as a New York City landmark, it certainly enjoys its status as one of the oldest bars in NYC.