Gritty 1920s illustration of an underground brick arched tunnel beneath the Strip District, lit by lanterns as shadowy figures roll whiskey barrels past damp stone walls and a ceiling trapdoor.

Bootleg Tunnels and Speakeasies Under Pittsburgh’s Strip District

Neighborhoods & Communities, Events & Turning Points

On a Tuesday afternoon in 1925, a federal Prohibition agent walking down Smallman Street would have seen nothing unusual. Produce vendors hawking vegetables. Freight trucks rumbling over cobblestones. Warehouse workers loading and unloading cargo along the Allegheny River. Then the agent would have noticed the door. Unmarked. Reinforced. A small sliding panel at eye level.…