The main street and its side alleys formed a red-light district where brothels, inns, "jilt shops", and taverns[3] could be segregated from the rest of the city.

[4] The establishments in the area relied heavily on custom from sailors, who had come ashore at Dock Square nearby, and working men, who used the taverns as meeting places in the winter.

It ran from Faneuil Market, spanned an old drawbridge, and led into the rest of the Boston's North End, terminating at the wharves.

The Ann Street area was occasionally subject to police raids, generally superficial affairs that left the brothels alone.

Police who patrolled the area (now known as the "Black Sea") estimated that it was home to 227 brothels, 26 gambling dens, and 1,500 establishments that sold liquor.