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.

This cemetery has graves dating back to the 17th century, including the city's oldest carved tombstone and an ominous cryptogram.

Try not to get slimed in Tribeca.

Salute the leader of the proletariat.

This 220-year-old house is a reminder of New York City's Dutch past.

The site of the deadly Triangle Shirtwaist Factory Fire.

Hidden in one of New York's oldest subway stations is the final remnant of the site of the bizarre Shakespeare Riots.

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

The former sign of this immortal music venue is just that--undying.

Plot your trip through the city on the sidewalk.

A terrific purveyor of natural history objects and curios.

Hollywood's most famous landmark, the "temporary" sign that has stood for decades longer than intended.

“Invented in Key West, Perfected in Brooklyn."

A decommissioned military complex that's now a modern industrial park.

The longest continuous underwater road in North America was built at the insistence of Franklin Roosevelt.

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

In its day this historic fort held 100 cannons pointed in almost every direction to protect New York.

Lie in a hammock where George Washington stood.

A museum devoted to bringing to light forgotten or neglected histories through exhibitions, education and public programming.

One of only two commuter aerial tramways in the United States.

A crumbling hospital from the 1850s on Roosevelt Island.

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

An alley way dedicated to graffiti and street art is a constantly changing street gallery.

This cemetery served as the only official burial grounds in Cambridge for nearly 200 years.