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.
Tour & Happy Hour at Pete’s Tavern
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.