8. Old Town Bar (1892)
Old Town Bar joined the Union Square neighborhood in 1882 as Viemeister’s. Like many of the other oldest bars in NYC on this list, it survived Prohibition by becoming a speakeasy under the name Craig’s Restaurant. During this stage in the bar’s history, patrons could hide their alcohol in a compartment underneath their seats.
Old Town opened as a German-style saloon that served only men at the bar, with an upper dining room where whole families could gather. It retains some of its decor from the 1930s as well as a pair of functioning 19th century Hinsdale urinals (which celebrated their 100-year anniversary in 2010). Though it has been popular in film, Old Town is also known as a literary bar—Frank McCourt, Billy Collins, and Nick Hornby are among the writers who frequented the high-ceilinged establishment.