A statue erected on an infamous cliff where young boys would hold dangerous "pee offs" to prove their mettle.

The oldest living tree in Manhattan comes shrouded in sinister legend.

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

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

The site of the deadly Triangle Shirtwaist Factory Fire.

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

Manhattan’s Battery Park has a whimsical carousel full of spinning, glowing fish.

Elevated freight railway turned wildly successful urban park.

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

Avoid gangster interaction while window-shopping.

The most confusing clock in New York.

Commemorating the spot where the famous scientist fed his pigeons.

A crumbling hospital from the 1850s on Roosevelt Island.

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

A little lighthouse in New York City, surrounded by mysterious stories of insanity-driven construction.

A former insane asylum despised by Nelly Bly and Charles Dickens is now fashionable apartments.

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

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

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 oldest surviving synagogue in New York City is now a soaring art space.

This former crime corner has been turned into an eclectic community center.

One of the few remaining American elm trees in New York’s Tompkins Square Park was the birthplace of a new religion.

Monument to a forgotten NYC disaster that claimed the lives of 1,000.