Must-See Flatiron District

NYCgo Staff

(Updated 08/06/2018)

Centered around lush Madison Square Park, the Flatiron District is a dynamic hub of food, shopping and culture rivaling that of prominent neighbors like Chelsea and Union Square. It’s an area filled with exciting history too, some of which remains visible today.

Its name comes from the Flatiron Building, a historic skyscraper that was one of the first steel-framed buildings in the City when it was built in 1902. Landmarked in 1966, its unusual shape makes it a draw for NYC selfies. At the southeast corner of Madison Square Park, the former Metropolitan Life Tower enjoyed a brief time as the tallest building in the world in the early 1900s. Meanwhile, the distinctive, gold-topped New York Life Building on the park’s northeast corner lies on the site of the first two incarnations of Madison Square Garden, a block-long entertainment complex that dazzled turn-of-the-century New Yorkers.

Flatiron Building. Photo: Julienne Schaer

Today the classic cast-iron and beaux-arts architecture gives the streets of the Flatiron their historic charm, and dovetails flawlessly with the shops, restaurants and nightspots that keep sprouting up. Visitors flock here to shop for clothes and housewares, line up at food trucks parked up and down Fifth Avenue and Broadway, and dine at some of the City’s finest restaurants. Read on to find the best spots for exploration.

View of Empire State Building from Flatiron District. Photo: Kate Glicksberg

How to Get There

The Flatiron District runs from 18th Street to 27th Street, between Lexington Avenue (or, in the southern reaches, Park Avenue) and Sixth Avenue. It’s easily accessible by subway, taking the R, W or 6 trains to 23rd Street, or by the M1, M2 and M3 buses that run down Fifth Avenue from Midtown and the Upper East Side (and up Fourth Avenue, Park Avenue South and Madison Avenue from the East Village).

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 formally opened in 1847 right before the neighborhood began to rapidly develop—its history, before and after that debut, is worthy of exploration. Today the Madison Square Park Conservancy, a public-private partnership, works hard to maintain the park’s flower-filled gardens and puts on an annual summer art display, special outdoor concerts and various cultural events. Some 50,000 daily visitors come to lounge on benches, let their dogs or kids run around in dedicated spaces or line up for a cheeseburger and “concrete” custard at the original Shake Shack.

The Clocktower. Photo: Nick Solares

High-End Cuisine

For the past few decades, the Flatiron District has been synonymous with some of the top dining experiences in NYC, especially local and organic New American cuisine. Eleven Madison Park, a three-star Michelin restaurant that ranked number one on a 2017 list of the top 50 restaurants in the world, features James Beard Award winner Daniel Humm's upscale American food in a stunning space with soaring ceilings and impeccable service. The Clocktower, in the old Met Life Tower (not to be confused with Midtown’s MetLife Building), puts a British twist on haute cuisine, with a menu from Michelin-starred chef John Atherton. Probably the biggest and best-known place is Eataly, an Italian food court and market with a rooftop deck, Serra by Birreria (the theme changes seasonally), for dining alfresco.

Junoon Restaurant. Photo: Jay Shetty

Elsewhere in the ’hood, Gramercy Tavern sources local ingredients for its seasonal menu. The ingredient-conscious category also includes Craft, a New American restaurant that cemented celebrity chef Tom Colicchio’s status (he had kicked off his career at Gramercy Tavern). Merakia puts a Greek spin on a New York steakhouse, with Aegean-accented meat and potatoes dishes. Get a taste of India at Junoon, a Michelin-starred restaurant with a contemporary take on Indian classics. On the lighter side, Obica is an eatery that focuses on serving fresh, classic Italian dishes in a relaxed, friendly atmosphere.

City Bakery. Photo: Joe Buglewicz

Cheap Eats

For every fancy restaurant in Flatiron, there's an equally delicious casual eatery. Zero Otto Nove is known for its crisp, Neapolitan-style pizzas, along with other regional favorites. The retro-style Hill Country Chicken does Southern food right, focusing on crunchy fried chicken, buttermilk biscuits and other comforting staples (pie milkshakes, anyone?). Eisenberg's Sandwich Shop 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 legendary; take a table in the café and watch the cheese makers while you sample the curds of their labor. And to touch on the final frontier of guilty cheese pleasures, we found the thinnest thin-crust pizza around at casual Tappo.


For a quick, tasty lunch or snack, hit the cafeteria setup at local standby City Bakery; think healthy homemade soups, quinoa salads and veggie burgers, along with its famous pretzel croissants and thick hot chocolate. In May and September, don’t forget to check out Mad. Sq. Eats. This biannual culinary pop-up market features roughly two dozen different restaurants, food trucks and bakeries serving the likes of lobster rolls, rice balls, Korean barbecue and ice cream sandwiches.

Flatiron Building. Photo: Tagger Yancey IV

Historic Sights

You would be hard-pressed to miss the iconic Flatiron Building. This triangular-shaped tower was built in 1902 to fit into the size of a small plaza—the plot of land it was built upon was called “Flat Iron,” thanks to its shape. At 22 stories high and only 6.5 feet wide at its vertex, the building remains a draw, attracting Instagrammers 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.

Courtesy, Museum of Sex

There are a couple museums worth checking out in the neighborhood, one aimed at children and the other definitely for adults. The National Museum of Mathematics, also known as MoMath, features lots of kid-friendly hands-on exhibits about how the wonders of math make the world go ’round. Over on Fifth Avenue, the Museum of Sex is, obviously, not for the young ones (all visitors must be 18 or over). In addition to their permanent collection, which examines the history and cultural impact of sexuality, there’s a fun cocktail lounge called Night Fever, which recreates the swinging ’70s in NYC.

Fishs Eddy. Photo: Francine Daveta


Dating back to its Ladies’ Mile heyday, this area has a long history of major retailers along the Fifth Avenue corridor. A few blocks south of the Flatiron Building 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 on Fifth to find chain favorites like H&M, J.Crew, Coach and Anthropologie.

But the area is best known for its abundance of home and design stores—all of which can be seen, along with other local business, on the official neighborhood website,, which has a handy map showing all local businesses. You'll find a large Restoration Hardware, Marimekko and a Poggenpohl, along with housewares destination ABC Carpet & Home, a two-building warehouse-superstore (one for carpets and one for home) that sells everything from luxury comforters and chandeliers to workout clothes and bracelets.

For something lighthearted and lighter on the wallet, head to Fishs Eddy, a quirky kitchen and home store selling kitschy and contemporary glassware, flatware, mugs, kitchen supplies and assorted accent pieces. Some of the finds here have a whimsical NYC theme, making for suitable gifts or souvenirs.

Abracadabra. Photo: Kate Glicksberg

Specialty Stores

In addition to big name stores, there are plenty of places catering to niche interests. Abracadabra is perhaps the wackiest of the bunch, selling costumes, wigs, novelty items and magic tricks with in-house designers to help you find the right outfit or prop. Aimed squarely at kids' hearts and minds is the 3,500-square-foot LEGO store, a toy heaven full of intricate sculptures made from the iconic plastic bricks, including an 8-foot-tall Statue of Liberty torch.

For adults, there's NY Cake & Baking Distributors, which has every baking tool imaginable for the pastry neophyte or TheGreat British Baking Show wannabe. Equestrians will like 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 & CDs, which has a collection of new and used vinyl records and CDs covering classical, rock, jazz and the avant-garde. Finally, shutterbugs will adore Adorama, a comprehensive photography store that’s a vestige of a time when the neighborhood teemed with photo studios.


230 Fifth. Photo: Michael Muraz


While not an all-night hot spot, the Flatiron District does offer an eclectic mix of upscale lounges, dive bars and everything in between. 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. If you're looking for a fancy place to watch sporting events, check out the blingy 40/40 Club, owned by hip-hop mogul Jay-Z.

On the more casual side, Susan Sarandon’s Ping-Pong lounge, SPiN New York, has 16 tables and occasional DJs. Or you can grab a draft and an oversize pretzel over 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. For an authentic English-style pub, stop by The Churchill Tavern for some hearty draughts and shepherd pies.

Dan White. Courtesy, The Magician at the NoMad

Arts and Entertainment

The Flatiron has entertainment for every type of interest, from music to magic. 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 lounge in the basement. The nearby Baruch Performing Arts Center is on the Baruch College–City University of New York campus, but all are welcome to attend its music, theater and dance shows. Sketch comedy and up-and-coming stand-up acts take the stage nightly at the Peoples Improv Theater (aka The PIT). At the Nomad Hotel, you can be amazed by Dan White’s tricks showcased in an intimate parlor magic experience, The Magician.

To explore, book a hotel near the Flatiron District and stay close to the action.