Top 8 Things to Do in NYC's Flatiron District

Named after the distinctive, wedge-shaped, Insta-famous Flatiron Building, Manhattan’s centrally located Flatiron District sits just north of the Union Square area, with neighborhood boundaries falling roughly between 18th and 27th streets from south to north, and Lexington (or Park Avenue, at its southern reaches) and Sixth avenues from east to west, with Broadway slicing through its core.

Crowned by the green respite of Madison Square Park, the historic quarter has taken on a distinctly more residential character in recent decades —with the top-rate restaurants to support it—after serving for much of its history as a primarily commercial neighborhood. A slate of monikers nodding to the waves of businesses it supported have come and gone over the years—it once contained portions of the so-called Ladies’ Mile (when it housed fashionable department stores along its avenues), the Toy District, the Photo District, the tech company-fueled Silicon Alley, and more recently, the Fitness District, for its bevy of fitness studios.

With a local feel that’s off the tourist track, there is still shopping aplenty here today, with loads of restaurants, bars, and hotels, too. But there are also some enticing and eclectic attractions in the mix if you know where to look. Here are eight fun things to do in New York City’s Flatiron District.

01 of 08

Check Out the Flatiron Building

Flatiron Building lit up at night

TripSavvy / Donghee Eim

The triangular “iron” shaped Flatiron Building (originally known as the Fuller Building) is the defining landmark of the neighborhood, set at the juncture of Broadway, Fifth Avenue, and East 23rd Street. One of the city’s most photographed buildings, the angular Beaux-Arts-styled structure, fronted with limestone and terra-cotta (and designed by architect Daniel Burnham), dates to 1902. While reaching 21 stories high (thanks to its then-revolutionary steel frame), it’s a mere 6.5 feet wide at its narrowest point.

The iconic structure’s function is primarily an office building, meaning it's closed to the general public, but there are some ground-floor shops to peruse, and visitors can also dip into the lobby to check out a selection of historic photographs and information panels displayed on the wall.

02 of 08

Kick Back at Madison Square Park

Photo credit: Barry Winiker / Photodisc / Getty Images

Situated at the northern edge of the Flatiron District, this urban oasis has been serving New Yorkers as public space since 1686, offering a green retreat today that spans nearly seven acres with welcoming green lawns, lovely gardens, park benches, a dog run, playground, and robust arts and cultural programming, too. Located between Fifth and Madison avenues, between 23rd and 26th streets, Madison Square Park frequently serves as a backdrop to rotating large-scale art installations, with more than 30 public sculpture exhibits put on display since its Mad. Sq. Art arm debuted in 2004.

Plus, you’ll find a lively calendar of free public programming, including concerts, art talks, horticultural tours, family-friendly events, and more, along with the biannual food market, Mad. Sq. Eats—though you can queue up to chow down within the park’s boundaries at any time of year via a satisfying burger and milkshake pairing from the ever-popular (and original) Shake Shack.

03 of 08

Admire Century-Old Architecture

A side view of the Flatiron building looking east down 23rd Street with the clocktower on the left.


Michael Godek/Getty Images 

Madison Square Park is the perfect perch to take in the surrounding century-old architecture, which goes beyond the striking Flatiron Building that’s situated on the southwest edge of the park. Around the perimeter, you’ll find elegant landmarks like the 41-story-high Met Life Tower (at the park’s southeast corner at Madison Avenue and 23rd Street) and an Italian Renaissance-style clocktower (inspired by the campanile in Venice, Italy) that was the world’s tallest skyscraper when it was completed in 1909. Of interest to visitors today, it houses the luxe New York Edition Hotel. 

Next door, the Art Deco Metropolitan Life North Building commands attention, too. It was planned as a 100-story tower, though, the onset of the Great Depression ensured it never reached those lofty heights; the functioning 32-story base (officially completed in 1950 and a working office building today) still shows off those grand aspirations.

Then there’s the Cass Gilbert-designed, 34-story-high, neo-Gothic New York Life Insurance Building (1928), which comes crowned with a gilded pyramid (it’s off the park’s northeast corner at 51 Madison Avenue). And don’t miss the New York State Appellate Division Courthouse (on Madison Avenue at 25th Street), with its Beaux-Arts design, Corinthian columns, and ornate statuary (it was completed in 1900).

Thanks to historic preservation, a stroll through the remainder of the neighborhood reveals a rich tapestry of Beaux-Arts and cast-iron architecture throughout. Another great vantage point to soak up the architectural landscape? Head atop the massive 20th-floor rooftop bar at 230 Fifth, where for the price of a drink, you can get a bird’s-eye view over the architecture of the Flatiron District and beyond.

04 of 08

"Mangia" at Eataly

NYC & Company / Kate Glicksberg

Food, glorious food. One step into Eataly's Flatiron shrine to Italy's culinary tradition (a venture backed by celebrity chef Mario Batali), and you'll embark on a certain love affair with food. For budget-crunchers it's not, but Eataly presents a veritable Disneyland for foodies, with a massive food emporium bringing together several different restaurants (including one within the rooftop beer garden), and seemingly endless sections dedicated to high-quality fare from a wide array of food groups and drink choices (including pastas, cheeses, breads, meats and sausages, wine, beer, and more). Whether you're looking for a quick snack, to prep for a meal back home, or to sit down to indulge in some full-on feasting, Eataly's got you covered.

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05 of 08

Get Flirty at the Museum of Sex

Museum of Sex: Top 8 Things to Do in NYC’s Flatiron District

Raymond Boyd / Michael Ochs Archives / Getty Images

It’s rare to hear a museum described as sexy, but then again, not every museum is the Museum of Sex. You’ll want to leave the kiddies behind at this adults-only temple to just how said kiddies are made, with a tantalizing 20,000-piece collection of vintage sex toys, erotic artwork and photography, clothing and costumes, and other assorted kinky artifacts, all displayed in an effort to document the historical and cultural role and portrayal of human sexuality. The museum puts on rotating exhibitions, as well as guided tours, special events, and lectures; there’s a museum shop, too, since nobody should leave town without a set of faux-fur handcuffs.

06 of 08

Visit the Theodore Roosevelt Birthplace

Theodore Roosevelt Birthplace: Top 8 Things to Do in NYC’s Flatiron District

NYC & Company / Kate Glicksberg

Decidedly more sedate than the Museum of Sex, but an interesting stopover all the same, is the Theodore Roosevelt Birthplace. You’ll find the site of Theodore Roosevelt’s—the first U.S. president to be born in NYC—boyhood home in a Flatiron District townhouse on East 20th Street. Open to the public as a National Historic Site, the Theodore Roosevelt Birthplace allows visitors, via period rooms and a museum, a glimpse into the life of the sickly child who would go on to rise the presidency.

Just take note: The building is a reconstruction of the original house, which was demolished for construction in the early 20th century; however, the furnishings within are mostly original, donated by Roosevelt’s family. While entry is free, visit to the period rooms is via guided tour only, which is granted on a first-come, first-served based.

07 of 08

Pop Into the Grand Masonic Lodge

Grand Masonic Lodge: Top 8 Things to Do in NYC’s Flatiron District

NYC & Company / Kate Glicksberg

One more thing to know about Theodore Roosevelt: He was a freemason, part of the storied fraternal organization that’s intrigued the masses for centuries as a sort of “secret society.” Indeed, Roosevelt, like more than a dozen other U.S. presidents and other illustrious figures throughout history (Harry Houdini, Mark Twain, and Mozart among them), was part of the historical order, of which visitors can learn more about via a visit to the Grand Masonic Lodge.

Established in 1782, the landmarked Grand Masonic Lodge is the headquarters and base for the governing body of the masons of New York State. Pop in for free public guided tours of the Grand Lodge Building and Masonic Hall (available every day but Sunday); the interiors come filled with stately rooms, ornate decorations, and a library and museum, too.

08 of 08

Crunch Numbers at the National Museum of Mathematics

Museum Of Mathematics: Top 8 Things to Do in NYC’s Flatiron District

NYC & Company / Kate Glicksberg

The Flatiron District certainly earns points for thinking outside of the box when it comes to its museums: Another one in the unusual mix—and the only one of its kind in the U.S.—is the creatively designed National Museum of Mathematics (MoMath). The small museum comes chockablock with interactive galleries and exhibits dedicated to showcasing how “mathematics illuminates the patterns that shape the world around us.” Kids and adults alike can learn about math by attempting to ride a bike with square wheels, taking a basketball shot, drawing on a digital canvas, and more.