2. Chumley’s, Greenwich Village

Photo courtesy Chumley’s

Chumley’s, the famed former speakeasy located on 86 Bedford in Greenwich Village, has been open since it started rebelling against prohibition in 1928. As a result of its long history and cloudy past, it has become a deep source of mysterious anecdotes—most of their validity still on shaky ground. However, as Cabe reports, it was in fact the hang out spot for William Faulkner, fathers of the beat generation authors Jack Kerouac and Allen Ginsberg, and French feminist author, Simone de Beauvoir, among 42 other writers of the era listed by Cabe.

Though a chimney collapsed in 2007, almost completely condemning Chumley’s, the bar was instead rebuilt and renovated to match its 1920s glamour. This includes a completely refurbished fireplace (though codes prevent it from being of any practical use,) the untouched front door (speakeasy peep-hole and all) as a result of its historical landmark status, along with 220 author photos and book jackets discovered during the repairs.

Signature drink: Chaplin (Scotch, chocolate ice cream and citrus notes).