10. Whitehorse Tavern (1880)

As spelled out clearly on their website, Whitehorse Tavern claims the title of the second oldest tavern in New York, at 139 years old. It got its start in the mid 19th century, catering to Irish communities in the Village. But it didn’t gain a real name for itself until the 1930’s, when the Whitehorse was swept up in the counter culture movement, and became a hub of leftist politics, writer’s circles, and cutting edge music. Over the years, its lineup of regulars has included musicians Bob Dylan and Mary Travers of Peter, Paul, and Mary.

As the favorite of writers with names like Jack Kerouac, James Baldwin, Norman Mailer, William Styron, Allen Ginsburg, and more, the Whitehorse, then known as “the Horse,” has a special place in the Village’s literary tradition. Graffiti in the bathroom reading “GO HOME JACK” is testimony to the many times Jack Kerouac was kicked out for drunken behavior. A portrait also hangs over the favorite seat of Dylan Thomas, who may have spent his last hours at the bar in 1953. The iconic culture paper, The Village Voice, also traces its roots back to conversations at the bar of the Whitehorse.

The tavern’s unique historical and literary significance became a case study in Jane Jacobs’ The Death and Life of Great American CitiesIn 1969, it was awarded a historic landmark designation, which has saved it from alteration several times. In May of this year, it reopened under new ownership with a new renovation. Today, its virtue still lies in adherence to its history, with a nostalgically-styled bar and mementos of the old days lining the walls.