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

The artist and New York City icon lived, worked and died in this converted carriage house owned by another iconic artist, Andy Warhol.

A drawbridge named for a potentially intersex Polish national who fought alongside George Washington during the American Revolution, and an example of "Pulaski Red".

There must be a pun in this haystack somewhere...

The most confusing clock in New York.

The site of the deadly Triangle Shirtwaist Factory Fire.

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

This exemplar of modernist architecture is meant to captivate and inspire students of the Cooper Union.

This historic address is home to the beloved ball and is an almost totally empty building among the most expensive real estate in the world.

Little Red Lighthouse under the George Washington Bridge.

Tucked away amidst some of the most famous addresses in the world is New York's only fraction of a street.

Lie in a hammock where George Washington stood.

An artist's cute bronze subway sculptures belie his violent artistic past.

Avoid gangster interaction while window-shopping.

This mosaic dedicated to John Lennon was tended for years by a Beatles super-fan.

Rummage through this sunken ship, but leave your scuba gear at home.

Named the fifth most beautiful building in America in 1885, this former courthouse boasts the best view in the Village.

Slyly buy a shake in the Parker Meridien lobby.

Wine bottle sculpture with a ship's stateroom inside.

Curious crustaceans support an obelisk from ancient Egypt that now stands in modern-day Central Park.

The oldest operating apothecary in the US has treated everyone from Thomas Edison to Mark Twain.

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

Plot your trip through the city on the sidewalk.

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