A posh members-only club with a literally dramatic history.

This former crime corner has been turned into an eclectic community center.

A former connection to City Island, it has been abandoned since the 1930s.

I fought the law and the precinct caved in.

Imagine having a street run right through your home, or better yet, a historic bridge three stories high.

One of the oldest Jewish cemeteries in the city, it is now overgrown with an urban forest.

A dark patch of the ceiling at Grand Central Terminal which was not restored is still stained brown by tobacco.

A good place to research the Freemasons, esoterica, occultism, and hermeticism.

A way to take your secrets to someone else's grave.

Holding the most bodies of any cemetery in the United States.

This futuristic airport terminal was abandoned for decades before reopening as a hotel—with a vintage plane of its own parked out back.

Once America's longest-manned military fort, now an abandoned hulk.

This sculpture by artist Fritz Keonig survived the 9/11 attacks and now stands as a monument to the victims.

Peek through the gates at this oasis from the city, full of Old English charm.

A bit of retro transportation flair preserved in the world's largest department store.

Once the tallest building in the world and the site of "the highest dinner ever held in New York" this building now holds the most expensive penthouse in the city.

One of the last Jazz Age "Wonder Theaters" in New York City.

The name of this famed hospital was once a byword for the horrors of medical and psychiatric care.

This unmarked and unloved Manhattan subway grate created one of the most iconic images in American cinema.

A masterpiece of LGBT art has been restored in what may now be the most valuable restroom in America.

A restaurant on Staten Island showcases a different grandmother’s cooking every night.

Whisper secrets in a busy station only to be heard on the other side of this acoustic arch.

A hip bar decorated with walls of golden skulls.

Under a glass sidewalk lie the remains of some of Manhattan's oldest buildings.