A very classy 1920s-era bar right in Grand Central Station.

A grand New York post office that is home to mailman Santas, scraps of postal history, and a pneumatic mail system.

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

Everyone from Mark Twain to Teddy Roosevelt has a pipe hanging from the walls of this historic chophouse.

Once a popular watering hole among longshoremen and shipyard workers, this neighborhood treasure spans more than 100 years of Red Hook history.

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

Great place to have a drink and a bite to eat in an atmosphere laden with New York's Bohemian past.

While it now takes more than a dime to open an account this historic Brooklyn bank still displays the opulence of the gilded age in which it was built.

A quiet and contemplative oasis in the middle of New York's bustle and riot.

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 innocent-looking townhome is actually a subway exit.

A cargo of beautiful music.

Wall Street has a new heroine, a bronze statue of a small but fierce girl.

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

Order scoops of pandan, lychee, and black sesame at this family-run institution.

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

Avoid gangster interaction while window-shopping.

Possible relics of the ancient Roman city are hidden in this restaurant's façade.

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

A public urinal so pretty, it was declared a national monument.

Three connected pink triangles memorialize persecuted gays and lesbians throughout history.

This expansive bridge in the Canadian wilderness was originally just built for friends.

This historic Victorian hotel has a scandalous history of affairs and murder.

The narrowest street in Canada was once a spot for dastardly doings, now a historic piece of Chinatown.