5. Pamela’s Court
Fans of the speakeasy Chumley’s will remember this wonderful courtyard, really a small passageway off Barrow Street. Though not in operation since the wall collapse in 2007, it nonetheless retains its lore amongst New Yorkers. The building has served many functions, first as a blacksmithery and later as a stop on the Underground Railroad before the Civil War, and a place for leftist radicals later. The great literary greats hung out in the speakeasy founded by Leland Chumley in 1922.