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.

The fanciest public restroom in New York City boasts fresh flowers, art, and a classical music soundtrack.

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

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

This whimsical group of statues is a favorite of children who love to climb all over Lewis Carroll's beloved characters.

Whisper secrets in a busy station only to be heard on the other side of this acoustic arch.

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

The "Seinfeld" diner.

Elevated freight railway turned wildly successful urban park.

A semi-scholarly approach to sex.

A crumbling hospital from the 1850s on Roosevelt Island.

The oldest family-run luncheonette in New York, last renovated in 1948, still serves food and drinks the old-fashioned way.

The real-life site of Ichabod Crane's infamous gourd attack.

Oldest existing church in New York and the inspiration for Washington Irving's "The Legend of Sleepy Hollow."

America's most famous museum of medical oddities is home to the remains of Albert Einstein's brain.

The world’s first penitentiary, meant to be humane, drove men insane.

Cryptid lake monster honored with its own monument.

The sweetest graveyard in the world is filled with headstones for dearly de-pinted ice cream flavors.

The world's only international cryptozoology museum is host to an unrivaled collection of mysterious objects.

The early 20th-century home features cutting-edge technology of the day, such as ammonia refrigeration and needle showers.

The highest point in the state of New Hampshire, and while unlikely "the worst weather in the world," it sure seems that way to hikers.

According to the experts at the Guinness World's Record office, this is the longest candy counter in the world.

Come for the gun-toting hillbilly madman, stay for the ice-cream loving basketball bears.

Even Henry David Thoreau found this glacial pothole irresistible.