This quiet house on Gay Street, built in 1827, was once a bustling speakeasy and the home of a mayor’s mistress.

Thanks to its name, this charming little street happens to be one of the city’s most photographed.  Alas, it was called “Gay Street” long before the word “gay” developed its present meaning. The street was most likely named in the manner of most Greenwich Village streets—after a person. Though Sidney Howard Gay, abolitionist and editor of the National Anti-Slavery Standard newspaper, would have been a good guess, he was still a boy when the first reference to “Gay Street” appeared. In all likelihood, it was simply named after some lesser-known individual with the same jolly last name.

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Gay Street is much narrower today than it was in the early-19th century—because it wasn’t even a real street! Rather than serving as a walking path, it housed stables for horses—the major means of transportation for the wealthy Village inhabitants at the time.

As the city grew north and the wealthy (and their horses) gradually moved uptown, the stables were converted into lower-income housing  for servants, many of whom were African-Americans. By the 20th century, most inhabitants of Gay Street were black—and many of them were musicians.

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During the Prohibition, the secluded Gay Street (a natural location for speakeasies) housed the somewhat theatrical buccaneer-themed Pirate’s Den, located at 12 Gay Street.

The Pirate’s Den was undoubtedly patronized by New York’s dapper Mayor Jimmy Walker, known as the Night Mayor or Gentleman Jimmy, who wrote Broadway tunes before assuming his mayoral post. Dapper and charming, he liked to party all night—a habit that affected his office hours; if he showed up at all it was seldom before noon. He carried scandalous affairs with “chorus girls,” enjoyed libations and speakeasies, and discouraged the police from enforcing Prohibition.  After the Pirate’s Den closed down, Mayor Jimmy Walker set up his mistress, Betty Compton—a  Ziegfeld Follies showgirl—to live in this house, turning it for all practical purposes into a second mayoral residence.

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Adding to the colorful history of 12 Gay Street, the Howdy Doody puppet was created in its basement by Frank Paris, who lived there at the time.

Perhaps unsurprisingly, the place is considered to be haunted. Screeching stairs, screams of pain, sounds of clinking glasses, occasional cooking smells have all been reported over time. Every once in a while one can even spot the image of a dapper gentleman wearing a top hat and tails. Appearing very polite and elegant, the ghost might just be the building’s ex-owner and New York City’s gayest (pun intended!) mayor, Jimmy Walker.