The former home of the reclusive "Weird Wendels" who dominated New York real estate a century before Donald Trump.

A reminder to choose water over wine since 1888.

The original Uncle Sam was actually a New York meatpacker who is buried under this historic grave.

Pulled from the rubble of one of the worst modern tragedies, a steel crossbeam became a symbol of hope for New Yorkers.

Amid the marketing blitz of modern Times Square is an elegant holdover from its showbiz glory days.

Once considered the height of medical modernity, this structure is now the oldest remaining component of Roosevelt Hospital.

This forlorn park is the result of a failed investment turned tax dodge.

The last living thing to come out of the rubble after 9/11 is now a symbol of hope and resilience.

During the 19th century, you could pay for violence off a prix fixe menu on this Manhattan street.

Revolutionary War casualties fill the only 17th century structure remaining in Manhattan.

Ever wanted the laymen's version of your credit card fine print?

Those belting out show tunes might not realize this piano bar marks the site where Thomas Paine died in 1809.

There are owls with glowing eyes in Herald Square.

The origins of midtown Manhattan's anachronistic wooden farmhouse remain a mystery.

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

The one-time epicenter of American songwriting is now a little remembered Manhattan commercial block.

This subterranean oyster house has been the pearl of Grand Central Station since 1913.

This New York holdover was built to provide housing for shopgirls and still does not allow men above the lobby.

The first piece of public art dedicated to LGBT rights.

A plaque immortalizes the spot where the early American spy said his famous last words: "I only regret that I have but one life to lose for my country."

A sewing machine tycoon built this miniature castle for the people and to beautify a lakeshore.

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

A prohibition era watering hole for the police.

Cheap pizza and all of your naughty bedroom needs housed in a stunning example of Art Nouveau architecture.