1. Cripplebush

530 Flushing Avenue (Nostrand Avenue), Brooklyn, NY
Field · Williamsburg · 1 tip

Whitney M.Whitney McNamara: Cripplebush, an incorporated settlement near the current intersection of Nostrand and Flushing, was absorbed by the village of Wallabout in 1830.

2. Hole-in-the-wall

280 Water Street (Dover Street), New York, NY
Playground · Downtown Manhattan · 1 tip

Whitney M.Whitney McNamara: Through the 1850s, until its closing in 1855, the Hole-in-the-wall saloon was widely known as "the most vicious resort in the city", with seven murders having occurred in a two month period.

3. Grapevine Tavern

463 6th Avenue (11th Street), New York, NY
Pub · 1 tip

Whitney M.Whitney McNamara: The Grapevine Tavern, which closed in 1915, was such a popular gathering spot that the phrase “I heard it through the grapevine” was coined as a reference to gossip and news exchanged by its patrons.

4. The Black & Tan

153 Bleecker (Thompson), New York, NY
Dive Bar · Greenwich Village · No tips or reviews

Whitney M.Whitney McNamara: In the late 1880s, the Black & Tan was one of the first saloons to cater to New Yorkers of all races. The establishment was violent enough that bartenders were armed with long dirks and bludgeons.

5. Bandit's Roost

59 Mulberry Street (Bayard), New York, NY
Rest Area · Chinatown · No tips or reviews

Whitney M.Whitney McNamara: Bandit's Roost was the designation for an alley at 59 1/2 Mulberry Street, notorious in the late 19th century as the center of an area indisputably controlled by criminal gangs.

6. Digger Free Store

264 E 10th St (Btwn 1st & A), New York, NY
Miscellaneous Store · East Village · No tips or reviews

Whitney M.Whitney McNamara: The Digger Free Store operated in 1967-68. As the name suggests, everything in the store was free. Asked why they were doing this, the founders replied with the enigmatic Digger motto: "Diggers do."

7. Stanley's Bar

551 E 12th St (at Avenue B), New York, NY
Bar · Alphabet City · 1 tip

Whitney M.Whitney McNamara: A hub for the Beat Generation in the early '60s. The Fugs first performances were here, and patrons included Ginsberg, Ed Sanders, Tuli Kupferberg, and Odetta.

8. The Whiskey War

275 Plymouth Street (btwn Gold & Hudson), Brooklyn, NY
Field · Vinegar Hill · 1 tip

Whitney M.Whitney McNamara: New York's "Whiskey War" peaked on Dec. 3rd, 1869, US Army troops were sent into Brooklyn's 5th Ward to shut down the whiskey distilleries that were commonly (and illegally) operated in the area.

9. The Last Opium Den in New York City

295 Broome St (btwn Forsyth & Eldridge), New York, NY
Bar · Lower East Side · No tips or reviews

Whitney M.Whitney McNamara: The last known opium den in New York City -- which was raided and shut down on June 28 1957 -- was a second-floor tenement apartment at 295 Broome Street.