New York City’s Prohibition era was one of its most colorful and law-defying chapters. On this walking tour through the Lower East Side, Little Italy, and Chinatown, you’ll trace how Prohibition transformed a city with roughly 15,000 saloons into a city filled with tens of thousands of illegal drinking establishments. You’ll also discover how that same law accidentally invented modern nightlife, the cocktail culture we know today, and a new kind of American woman.

The tour starts at Tompkins Square Park in the East Village, where a Temperance fountain – installed to encourage people to drink water instead of whiskey – sets the scene perfectly. From there, you’ll walk through neighborhoods shaped by successive waves of immigration, from the German enclave of Kleindeutschland to Little Ukraine, passing legendary institutions like Katz’s Delicatessen and Russ & Daughters along the way.

The route winds through the Lower East Side and into Chinatown’s Doyers Street, where you’ll discover both modern speakeasy-style bars and The Back Room – one of the rare surviving New York establishments that actually operated as a speakeasy during Prohibition. Hidden behind an alley and accessed through an unmarked entrance, The Back Room was used by gangsters – Meyer Lansky, Lucky Luciano, and Bugsy Siegel – as a meeting spot. You’ll hear how the world of bootlegging helped transform American organized crime. The tour ends near Apotheke on Doyers Street’s infamous Bloody Angle, an apothecary-themed bar housed in a building long rumored to have once contained an opium den.