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Flatiron Food and History Tour
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17 things you can only do in NYC

Where else in the world could you drink at a Revolutionary War–era bar and visit the country’s first sex museum in the same day?

Annalise Mantz
Written by
Annalise Mantz
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There’s really no place in the world quite like New York City. Thanks to its dense population (one in every 38 people in the United States live here) and storied history, NYC offers plenty of things to do you won’t find anywhere else. Whether you’re a local or only here for a few days, don’t squander your time on run-of-the-mill attractions. To discover the most unique parts of the city, you have to tear yourself away from the best New York attractions to go off the beaten path. You might even uncover some of what locals call the secret New York while you’re at it. As the saying goes, when in Rome…

RECOMMENDED: Full guide to the best things to do in NYC

Things you can only do in NYC

  • Bars
  • Beer bars
  • Financial District

Samuel Fraunces first purchased the property at 54 Pearl Street in 1762, and revelers have been drinking their cares away at Fraunces Tavern ever since. There’s plenty of history within these hallowed halls: British forces shot a cannonball through the roof in 1775, George Washington raised a glass here on several occasions and the bar even served as the headquarters of the Department of Foreign Affairs for a time. Whether your order one of Fraunces Tavern’s 140 craft beers or 200 whiskeys, make sure you raise a glass to the revolution!

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New York is the most linguistically diverse city in the world, with more than 800 languages spoken across the five boroughs, according to Endangered Language Alliance. Nowhere is this more obvious than in Queens, where you can hear snippets of Urdu, Croatian, Javanese and Coptic over the span of a few blocks. Explore the beautiful mosaic of neighborhoods that make the borough so diverse on a walk through the neighborhood.

  • Restaurants
  • Hot dogs
  • Coney Island

There’s some disagreement among hot dog historians about where the favorite ball-park food originated, but many claim that German baker Charles Feltman first sold them at a Coney Island stand in 1871. Guess who worked for Feltman? Nathan Handwerker, who opened his eponymous sausage business a few years later. Order up one of the snappy all-beef dogs at the original stand on Coney Island—and take a spin on the Cyclone while you’re there.

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  • Attractions
  • Libraries, archives and foundations
  • Midtown West

Winnie-the-Pooh, Piglet, Eeyore and the other characters from the beloved children’s books really are real—or at least, real stuffed animals. Author A. A. Milne got his inspiration for the series from his son Christopher Robin’s collection of toys, all of which are now on display at the New York Public Library’s Children’s Center. Seeing the well-loved bear bought at Harrods in London in 1921 almost feels like stepping into the Hundred Acre Wood.

Sorry folks: If it’s not in New York City, it’s not Broadway. Even if your home town has the most gorgeous, 900-seat theater that hosts only the best touring companies, it doesn’t count. To see a real-deal Broadway show, you have to do it here. Whether you shell out the big bucks for Hamilton or go for a newer addition, like The Notebook, you'll be amazed at the caliber of the production.

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  • Clubs
  • Lenox Hill

Like many New York social clubs, the Explorer’s Club holds an annual gala and dinner. The menu, though, isn’t the usual filet mignon and caesar salad. Past dinners have included everything from fried tarantulas to goat eyeballs. Though the club only offers membership to a select group of adventurers—think Neil Armstrong and James Cameron—the annual gala is open to anyone who can afford the (pricey) tickets.

  • Shopping
  • Department stores
  • Midtown West

With 11 floors and more than 1.2 million square feet of retail space, Macy’s Herald Square location is the largest department store in the country and one of the largest in the world. Come in December to catch a glimpse of the famous holiday windows or in the spring to peep the annual flower show. No matter what time of year you visit, you can always count on an dazzling experience. Be sure to head upstairs to ride on the original wooden escalators.

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  • Restaurants
  • American
  • Financial District

Despite this dessert’s name, baked Alaska wasn’t invented in the frozen territory to the north, but at Delmonico’s in the Financial District. The United States’ acquisition of Alaska from Russia in 1867 inspired pastry chef Charles Ranhofer to create the dessert he called “Alaska, Florida”: walnut spice cake topped with banana ice cream covered in a layer of torched meringue. The dessert originally sold for the equivalent of $40, since it required the help of the entire kitchen staff to create. Thankfully, the advent of modern culinary equipment has brought the cost of today’s version down to $24.

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Stand on one of the smallest pieces of privately held real estate
Photograph: Courtesy CC/Flickr/Jason Eppink

11. Stand on one of the smallest pieces of privately held real estate

When the city extended the 7th Avenue subway line into Greenwich Village in the early 1900s, about 300 buildings were condemned and demolished to make room.

One landlord—David Hess—didn't give up so easily, though. Somehow, city surveyors missed a tiny, 500-square-inch triangle of his property. The Hess family seized the opportunity, covering the triangle in a tile mosaic that reads “Property of the Hess Estate Which Has Never Been Dedicated For Public Purposes.”

Though a neighboring business eventually purchased the Hess Triangle for $1,000 in 1938, you can still visit this reminder of one landlord’s determination.

Eat endless different types of pizza in one day
Photograph: Shutterstock

12. Eat endless different types of pizza in one day

With thousands of pizzerias in this city, there’s no shortage of different varieties: classic New York-style, thick Sicilian-style, wood-fired, coal oven, Neapolitan, Roman, the list goes on and on. You could spend years working your way through every slicery in the five boroughs and still not taste it all. To get the ultimate pie-tasting experience, book a pizza walking tour to enjoy samples from the some of the city’s best pizzerias in one go.

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  • Museums
  • Art and design
  • Washington Heights

At the northern tip of Manhattan, footpaths wind through Fort Tryon Park to what appears to be a castle from Medieval times: the Cloisters. In actuality, this museum dedicated to the art of the Middle Ages was built less than 100 years ago, though the architects did use material from five medieval French cloisters. The incredible architecture and awe-inspiring artifacts—including the famed unicorn tapestries from John D. Rockefeller Jr.’s collection—have to be seen to be believed.

Pull up a bar stool at the former hangout of Jack Kerouac and Bob Dylan
  • Bars
  • Pubs
  • West Village

History buffs probably already know about White Horse Tavern’s literary legacy: Welsh poet Dylan Thomas died after allegedly pounding 18 shots there and Jack Kerouac was kicked out so many times that one annoyed patron scrawled “Go home Jack!” on the bathroom stall. You can still see that graffiti and soak up the ambiance on a visit to the legendary pub today.

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Spot the filming locations of hundreds of TV shows and movies
Photograph: Courtesy Breakfast at Tiffany's

16. Spot the filming locations of hundreds of TV shows and movies

So many movies and TV shows have been filmed in New York City that we’ll probably never have a complete tally. Sure, NYC's streets might never measure up to L.A.’s enormous studio lots, but we come pretty damn close. Find the locations of Breakfast at Tiffany’s, Moonstruck, Friends, Almost Famous and other classics around town.

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Ride the biggest subway system in the United States
Photograph: Shutterstock/Allen G.

17. Ride the biggest subway system in the United States

All New Yorkers will inevitably hear some tourist chattering about how excited they are to ride the subway while commuting and want to punch them. But really, once you look past the “It’s showtime!” people and lingering smells, the subway is something of a modern wonder. Take a private underground tour to learn the subway’s fascinating history and even spot some often-overlooked art.

Ready to explore more of the city?

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