A 19th century hat factory still stands as a crumbling ruin in upstate New York.

This island castle contains enough secret passageways to support a season of Scooby-Doo episodes.

This tiny little island has, as the name says, just enough room for its single house.

A castle built for love, and abandoned due to heartbreak.

The private island of Yale's elite Skull & Bones society is kind of a dump.

Crammed into several rooms of a Staten Island home, this museum is a vodka-soaked paean to the pleasures of drinking.

A dark, dank room in subterranean Manhattan was the site of a ghastly murder.

A remnant from the golden age of aviation still in use today, Pan Am's Clipper service took off from this Art Deco gem.

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

The Vatican of the movie industry turned into an actual church.

Where now stands a 42-story condominium tower of marble, glass and steel was once the central market of New York’s slave trade.

A strangely angled West Village home is the only monument to an explosion that took the lives of three American revolutionaries.

Walk into the 19th century without leaving Brooklyn.

Abandoned 19th century homes once occupied by naval officers, soon to be demolished.

The site where Joe Gallo kept his guns, pet lion, and launched an all out mob war in 1960s Brooklyn.

Touching mementoes from those who didn't make it back from World War I still hang in one of New York's oldest bars.

A clock set into the concrete outside a Manhattan jeweler has been telling time underfoot for over a century.

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

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

A dilapidated dock tells the story of Titanic's missed arrival.

New York City's smallest piece of private property.

Try not to get slimed in Tribeca.

One of the deadliest American air disasters is nearly forgotten in Brooklyn.

The legendary court where emerging basketball players gain their street cred.