Must-See Flatiron District

Alyson Penn


One hundred years ago, the Flatiron District was a major commercial and residential hub in the City. The Met Life Tower enjoyed a brief time as the the tallest building in the world; a flock of influential people called the neighborhood home; and large department stores drew big crowds of well-heeled patrons. While the area began to fade around the mid-20th century, the bones for its reemergence in the late 1980s and 1990s remained intact. Today, the cast-iron and beaux-arts architecture gives the streets their historic charm and dovetails flawlessly with the new shops, restaurants and nightspots that keep sprouting up.

Frequently described as a neighborhood reborn, the Flatiron is filled with a palpable vigor from those who flock here to shop for clothes and housewares, line up at food trucks parked up and down Fifth Avenue and Broadway, stock up on sumptuous Italian treats at Eataly—and naturally, to snap photos of the triangular Flatiron Building, which anchors it all.

But all the enthusiasm and visiting hordes haven't wiped out the strong sense of community embraced by locals, who love hanging out in Madison Square Park, greeting neighbors at the playground or dog run or simply watching a summer sunset against the urban backdrop.

Flatiron District Flatiron District. Photo: Julienne Schaer

Where it is
The Flatiron District runs from around 18th Street to 27th Street, between Lexington Avenue (or, in the southern reaches, Park Avenue) and Sixth Avenue.

How to get there
Take the N, R or 6 trains to 23rd Street.

To explore more, book a hotel near the Flatiron District so you can stay close to the action.

Madison Square Park Madison Square Park. Photo: Marley White

Madison Square Park

The heart of the Flatiron District is Madison Square Park. Bounded by Madison Avenue, Broadway and Fifth Avenue between 23rd and 26th Streets, the park, a former potter's field, formally opened in 1847 and for years enjoyed its place as one of the City's premier verdant oases. (The first two iterations of Madison Square Garden, built in 1879 and again in 1892, sat adjacent to the park.) By the 1970s, however, the park had fallen into a state of neglect; though restoration work began in the 1980s, it wasn't completed until around the turn of the century, when the park once again became known as a welcoming destination.

The Madison Square Park Conservancy, a public-private partnership, works hard to maintain the park's vitality and appeal. It brings in food-truck events and Oval Lawn concerts, while keeping up the flower-filled gardens and grassy grounds. Some 50,000 people visit daily to lounge on benches, run their dogs or kids around, or line up for a “concrete” custard at Shake Shack, in the southeast corner.

ABC Kitchen ABC Kitchen. Photo: Tagger Yancey IV

High-End Cuisine

For the past 15 years, the Flatiron District has been synonymous with some of the top dining in New York City, especially within the rubric of local and organic New American cuisine. One of the best-known players is Eleven Madison Park, a three-star Michelin restaurant that ranked third on a 2016 list of the top 50 restaurants in the world. Enjoy James Beard Award winner Daniel Humm's upscale American food in a setting that features soaring ceilings, elaborate floral displays and impeccable service. Another popular spot is the Gramercy Tavern, which sources local ingredients for its seasonal menu: look for starters like cauliflower cappelletti with currants and American caviar and entrees such as sea bass, parsnips, wild rice and lobster sauce.


ABC Kitchen, the hot spot that Jean-Georges Vongerichten opened in 2010, has a similar approach to its cuisine: dishes on the rotating menu might include pretzel-dusted calamari or akaushi (a type of wagyu beef) cheeseburgers; enjoy them in airy, rustic surroundings. The ingredient-conscious category also numbers Craft, the New American restaurant that cemented celebrity chef Tom Colicchio's status (after he had been a partner in Gramercy Tavern). Its focus is on simply but perfectly cooked greenmarket fare. For a modern twist on Mexican, try Cosme, the newish restaurant from chef Enrique Olvera that sources ingredients from New York's Hudson Valley and offers menu favorites like duck carnitas, meant for sharing, and crispy octopus with hazelnut mole and pickled potatoes.

Shake Shack in Madison Square Park Shake Shack, Madison Square Park. Photo: Alex Lopez

Cheap Eats

For every fancy restaurant in the Flatiron there's an equally scrumptious casual eatery. Shake Shack is a Madison Square Park staple, of course, with incredible cheeseburgers, shakes and fries and outdoor seating that is illuminated by strings of lights at night. The retro-style Hill Country Chicken does Southern food right, focusing on crispy fried chicken, buttermilk biscuits and other comforting staples. Eisenberg's Sandwich Shop, a few blocks away, has been slinging classic New York City diner food in the neighborhood since 1929, and is revered by locals for its stellar tuna fish sandwich. Meanwhile, the grilled cheese and mac and cheese at Beecher's Handmade Cheese are not to be missed; take a table in the café and watch the cheese makers at work while you sample the fruits of their labor. And to touch on the final frontier of guilty pleasures, we found the thinnest thin-crust pizza around at casual Tappo, home to mouthwatering pies at reasonable prices.

Neighborhood standby City Bakery is set up cafeteria style for a quick, tasty lunch or snack; think homemade soups, quinoa salads and veggie burgers on the healthy end of the spectrum and its famous pretzel croissants and decadent thick hot chocolate on the other (order a 2-ounce “shot” to sample its frothy goodness). KOA is a recent addition to the neighborhood, dishing up their own healthy noodle bowls called “sorba”—like ramen, but with less broth and more toppings—along with other creative Chinese dishes. And don't forget to check out the twice-yearly Mad. Sq. Eats (May and September). The culinary pop-up market, which sets up next to the park, features 30 different restaurants, food trucks and bakeries serving the likes of lobster rolls, rice balls, Korean barbecue and ice cream sandwiches.

Theodore Roosevelt Birthplace in NYC Theodore Roosevelt Birthplace. Photo: Malcolm Brown

Historic Sights

Long before Fifth Avenue earned its name as the shopping destination of New York City, there was Sixth Avenue in the Flatiron. It served as the western boundary of so-called Ladies' Mile, the onetime fashion center of the City thanks to the influx of department stores on Broadway and Sixth Avenue from the mid-19th century to the early 20th century. Upper-class women dressed in their finery would head out to shop along these streets, where the stores occupied beaux-arts, neo-Renaissance and Romanesque revival buildings; the area was eventually designated the Ladies' Mile Historic District in 1989.

You would be hard-pressed to miss the iconic Flatiron Building in heart of it all. The triangular-shaped structure was built in 1902 to fit into the size of a small plaza (contrary to popular belief, it was not the world's first steel-frame skyscraper, nor was it ever NYC's tallest building; as for the name, the plot of land it was built upon was called “Flat Iron,” thanks to its shape, before the building was constructed). At 22 stories high and only 6.5 feet wide at the vertex, the building remains a major draw, attracting tourists hoping to snap a pic from the perfect angle. While you can't tour the upper levels of the building, you can enter storefronts on the ground floor, including MAC Cosmetics and Argo Tea.

Built contemporaneously, the Grand Masonic Lodge is a 19-story home base for the fraternal organization. Since its opening in the Flatiron District, the lodge has seen many famous faces come and go, including members Harry Houdini, Irving Berlin and Eddie Cantor; you can find pictures of them outside the rooms in which they attended meetings. It's open for free public tours by expert guides who will recount the history of a dozen lodge rooms, each ornately decorated to a different motif. Be sure to head to the library and ask to see a handwritten letter by George Washington to fellow Masons.

The neighborhood holds another site honoring a president who was a Mason, but the Theodore Roosevelt Birthplace is closed for renovations until late summer 2016. The reconstructed brownstone is built where TR spent his childhood and decorated in period furnishings—including many actual pieces from Roosevelt's early years. Check for the latest progress report.

During your wanderings in the neighborhood, you probably passed right by a marked gravesite without even knowing it. That 51-foot obelisk on 24th Street and Broadway indicates the burial place of General William Jenkins Worth, who fought in the War of 1812, the Seminole Wars and the Mexican-American War.


Fishs Eddy Fishs Eddy. Photo: Francine Daveta


In terms of being a shopping magnet, little has changed in the Flatriron since the Ladies' Mile days. A few blocks south of the Flatiron Building on Fifth Avenue is Club Monaco, which has been renovated to include Toby's Estate Coffee, a cozy, airy café, and a mini outpost of the Strand Book Store, the Union Square institution. Keep heading downtown to find well-known favorites like H&MJ.CrewCoach and Anthropologie, as well as treasures on side streets along the way.

But the Flatiron is perhaps best known for its abundance of home and design stores (39, according to the district's official website, You'll find a large Restoration Hardware, Marimekko and a Poggen Pohl, along with housewares mecca ABC Carpet & Home, a two-building warehouse-superstore (one just holds carpets) that sells everything from luxury comforters and chandeliers to workout clothes and bracelets.

For something lighthearted (and lighter on the wallet), walk one block up from ABC Carpet & Home to Fishs Eddy, the quirky kitchen and home store seling kitschy and contemporary glassware, flatware, mugs, kitchen supplies and assorted home decor; pieces often have a whimsical NYC theme and make for good gifts or souvenirs.

Abracadabra Abracadabra. Photo: Kate Glicksberg

Specialty Stores

While there is a great variety of chain stores in the area, there are also plenty of places catering to particular niche interests. Abracadabra is perhaps the wackiest of the bunch. The 30-year-old store, which has called the Flatiron home for 15 years, sells costumes, wigs, novelty items and magic tricks. The megastore has in-house designers that can help you find the right fright outfit or prop material, and it also sells products from local designers, giving the shop more of a community feel.

Aimed squarely at kids' hearts and minds is the 3,500-square-foot LEGO store, a toy heaven full of intricate Lego sculptures (including the evolution of the Flatiron District), an 8-foot-tall Statue of Liberty torch and the “Pick a Brick” wall full of individual pieces.

For the adults, there's NY Cake & Baking Distributors, which has every baking tool under the sun for the pastry neophyte or the Dominique Ansel wannabe. If you fancy yourself more of a Magellan, navigate over to Idlewild Books, which sells travel-related publications and offers language classes as well. Equestrians love Manhattan Saddlery, the only tack shop (a place that sells harnesses and other stable gear) in New York City, in operation since 1912. Music lovers shouldn't miss Academy Records, which has a collection of new and used vinyl records and CDs covering classical, rock, jazz and the avant-garde; movies on DVD are also available. Finally, shutterbugs will adore Adorama, a comprehensive photography store that's a vestige of a time when the neighborhood teemed with photo studios and boutique ad agencies.

The Jazz Standard The Jazz Standard. Photo: Kate Glicksberg


While Flatiron might not be a raging late-night hot spot, it still has an eclectic mix of upscale lounges, dive bars and places in between. The Gansevoort Park Avenue replicates the stylish vibe of its Meatpacking location a little farther west: its popular rooftop bar attracts a fashionable crowd undeterred by the picky door policy and pricey drinks. Continue the party at SPiN New York, Susan Sarandon's Ping-Pong lounge with 17 tables and live music on the weekends. 230 Fifth is the place to go if you want great views year-round. The rooftop has front-row seats for seeing the Empire State Building, and in the winter the bar provides snuggies so you can enjoy your drinks in relative warmth.

For a quiet date or a catch-up with friends, check out the Flatiron Lounge. The deco-style cocktail establishment harks back to the 1920s and '30s, with jazzy music, a vintage bar and a changing menu of carefully crafted cocktails. The Jazz Standard (in the basement of Southern-food oasis Blue Smoke) also exudes an elegant vibe with a daily schedule of live jazz performances. While there are no drink or food minimums, you have to buy tickets to see a show.


On the more casual side, you can grab a draft and an oversize pretzel at Flatiron Hall, a beer hall and restaurant with vintage flair. Seating on the bottom level is all long benches, good for socializing with a big group or making new friends. Right across from Madison Square Park is shack-like Live Bait, where you can find local office workers indulging in happy-hour specials.

If you're looking for a fancy place to watch games, check out the 40/40 Club, owned by Jay Z. Its various levels are filled with oversize projection screens and TVs displaying the day's sporting events, and a full menu is available.

Eataly Eataly. Photo: Virginia Rollison


You can't go to the Flatiron without visiting New York City's very own indoor piazza, Eataly. The Italian marketplace, a hybrid space for shopping and eating, opened to a flurry of media attention in 2010 and has managed to live up to all the hype. While it can be tricky to navigate through mobs of tourists and locals at pretty much any hour, the vast selection and supreme quality of the food make it a worthwhile adventure.

Located in the 58,000-square-foot complex are seven restaurants that each have their own theme, including Il Pesce (fish and seafod), Le Verdure (vegetables), La Piazza (salumi and formaggi) and La Pizza & La Pasta (pizza and pasta, of course). Eataly's market is stocked like a grocery store, with shelves full of olive oil, bags of pasta and refrigerators full of cheese, along with specialty and handmade items like fresh squid-ink tagliatelle and seasonal spring-pea ravioli at the pasta counter or roast meat sandwiches in the Rosticceria. Additionally, you'll find an espresso bar, a gelato counter, a pasticceria, a wine shop and even a book section.

Then there's the roof. A quick elevator ride takes you up to Birreria, the rooftop bar and restaurant that has house-brewed ales on tap, a full food menu and great views of the nearby park. And just in case you were wondering what else Eataly offered, year-round events include cooking classes, kids' tours and conversations with food luminaries.

National Museum of Mathematics. National Museum of Mathematics. Photo: Kate Glicksberg

Arts, Culture and Entertainment

The Flatiron has entertainment for every type of interest. Musical groups of every genre are booked at the Gramercy Theatre, which has a mix of standing room and theater seating in the main space and a more intimate lounge in the basement. The nearby Baruch Performing Arts Center music is on the Baruch College campus, but all are welcome to attend its music, theater and dance shows. Sketch comedy and stand-up acts take the stage nightly at the Peoples Improv Theater.

For the kids (and the math nerds) there's the National Museum of Mathematics, where interactive exhibitions bring the subject's everday applications to life. But definitely leave the young ones at home for a visit to the Museum of Sex, which attempts to shine a light on human sexuality's role in different cultures and eras. The permanent collection features vintage sex toys, erotic paintings and a selection of French postcards that a century ago would no doubt have brought a blush to the countenance of those fine perambulators on Ladies' Mile.


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