Unrepaired walls from a 1920 anarchist bomb attack.

There are owls with glowing eyes in Herald Square.

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

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

This city park was once a lookout point for George Washington’s army during the Battle of Brooklyn in 1776.

This enormous banquet-themed artwork honors over 1,000 notable women throughout history.

This innocent-looking townhome is actually a subway exit.

The Underground Railroad passed right through this historic Brooklyn Heights church.

There must be a pun in this haystack somewhere...

A small peaceful park and waterfall tucked amid the urban grind of Midtown Manhattan.

Though the case is scorched and the buttons half-melted, this hardy handheld gaming device can still run a game of Tetris.

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

New York's unstoppable progress turned this cemetery into the smallest burial ground in the city.

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

Named the fifth most beautiful building in America in 1885, this former courthouse boasts the best view in the Village.

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

Jimi Hendrix's legendary recording studio in Greenwich Village.

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

The site of the deadly Triangle Shirtwaist Factory Fire.

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

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

Spiral-bound community recipes and antiquarian gems mingle at this small East Village shop.

Love, knishes, and best wishes from this legendary Lower East Side bakery.

The competition: breathe deeply as long as you can.