1. Washington Square Park
Next time you’re watching old dudes play chess or rushing past the fountain to get to class on time, remember that there are over 20,000 bodies buried beneath Washington Square Park. That particular plot of land has a many-storied, egregious past steeped in slavery and false promises when it was used as 17th Century Dutch farmland, and after that cheery past, it become a public burial ground for everyone from Jane Does to poor people who couldn’t afford a proper burial to victims of the 19th Century yellow fever epidemics.
2. Union Square
That mess of numbers south of Union Square is actually a clock. No, really, I know it’s not going to help you tell time when you’re stumbling home drunk at 3am, but it’s totally a clock — an art installation actually: The Metronome created in 1999 by Kristen Jones and Andrew Ginzel. You can figure out the time by thinking of it as sort of a digital hourglass: The first seven numbers represent the time that has passed since midnight (e.g. 19h42m38s) and the last seven numbers represent the time yet to pass until midnight (e.g. 62s57m04h) with the middle number constantly fluctuating.
3. The High Line
Long before it became Manhattan’s park in the sky above The Meatpacking District & Chelsea, The High Line was an elevated freight train line known as the Lifeline of New York, delivering goods from the harbor to such warehouses as Nabisco Biscuit Company (now Chelsea Market). Originally, those trains ran along street level, but in the ’30s the city decided to elevate the line directly through buildings when street traffic had become so dangerous that Tenth Avenue had long been nicknamed “Death Avenue.” Their first solution was a bit of a bust anyway: West Side Cowboys a.k.a. basically crossing guards on horseback rode in front of the freight trains, waving red flags or red lanterns to warn people away from the oncoming danger. Seriously, that was their solution for more than 80 years: cowboys.
4. McSorley’s Ale House
The oldest bar in New York City had a strict policy of not admitting women until as late as 1970 — and even then, they had to be court-ordered to let women through their doors. Before the ’70s though, legend has it that a couple of women tried to crash the men’s only pub party: Vaudeville performer Maggie Cline, who dressed as a man, ordered the McSorley’s two half-pints, and then went, “Ha ha ha! I’m a woman! Suck it, sexists!” and Wonder Woman herself, who basically did the same thing.
5. Jefferson Market Library
You’ve probably mistaken this Art Deco public library on Sixth Avenue for a church or even a castle, but this West Village landmark was originally a courthouse that eventually transformed its neighboring market into the Women’s House of Detention. This women’s prison (now the site of a gorgeous gated garden) was famous for cases such as Mae West’s obscenity charge for her Broadway play Sex or Valerie Solanas’s attempted-assassination charge when she shot Andy Warhol. Rumor has it that inmates would often pass the time by reaching through the bars of their cells and catcalling down at men walking past below.
6. Gramercy Park
At the heart of Manhattan’s only private park (you need to live adjacent and pay a pretty steep fee to earn a key) lives a statue of Edwin Booth as Hamlet. Of course, the Booth that most famously went down in history was John Wilkes, Lincoln’s assassin, but Edwin’s loyalties rivaled his brother’s, and he is considered by many theatre historians as the 19th Century’s greatest Shakespearean actor. This statue of Booth was even the first statue of an actor ever displayed in Manhattan.
7. Flushing Meadows—Corona Park
Not one but two World’s Fairs were held up in Queens (1939 and 1964), and the ruins of those events still stand today. Most of us recognize the Unisphere and the New York Pavilion’s Observation Towers from the final showdown in Men in Black, but there are so many more pieces of history tucked away at Flushing Meadows: time capsules (included in 1968: a checkered bikini, “A Hard Day’s Night” Beatles record, birth control pills, an electric toothbrush), Dalí and Warhol mosaics, and in the recently-renovated Queens Museum of Art, the Panorama of New York. That last one is something every New Yorker needs to see at least once: a built-to-scale comprehensive map of the five boroughs that fills out the floor of a darkened room where you can observe on pathways from above and even spot a replica of your apartment building if it’s been around since the ’60s.
Today, brownstones are often a symbol of gentrification, but 19th Century architects built the upstairs-downstairs division in brownstones that way to bring the upper class above the literal shit the lower class had to deal with. Remember how transportation was mainly horse-and-buggy back then? When it rained in the city, piles of horse manure would flood the streets and sidewalks and seep into ground-level apartments.
9. The Intrepid Sea-Air-Space Museum
You might know the Intrepid as a cool outdoor movie spot in the summer, but its real claim to fame is much more harrowing: A man by the name of Benjamin Franklin Gates once escaped from the FBI by jumping from the flight deck of the USS Intrepid. His mission? To decode clues in the Declaration of Independence that led to a secret national treasure hidden beneath the city.
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