Gramercy and Flatiron guide: The best of the neighborhood

Find the best restaurants, events, bars, shops, attractions and things to do in Gramercy and Flatiron in Manhattan.

Flatiron Building

Taking its name from the distinctive wedge-shaped Flatiron Building, the Flatiron District extends from 14th to 30th Streets, between Sixth and Park Avenues. Initially, it was predominantly commercial, home to numerous toy manufacturers and photography studios. In the 19th century, the neighborhood went by the moniker of Ladies’ Mile, thanks to the ritzy department stores that lined Broadway and Sixth Avenue. These retail palaces attracted the “carriage trade,” wealthy women who bought the latest imported fashions and household goods. By 1914, most of the department stores had moved north, leaving their proud cast-iron buildings behind. By the turn of the millennium, many Internet start-ups had moved to the area, earning it the nickname “Silicon Alley.”

RECOMMENDED: Full coverage of things to do in Manhattan

The Gramercy neighborhood surrounds Gramercy Park—the tranquil, gated square at the bottom of Lexington Avenue between 20th and 21st Streets. A key to the secluded green space, which was developed in the 1830s to resemble a London square, is one of the most sought-after treasures in all the five boroughs. For the most part, only residents of the beautiful surrounding townhouses and apartment buildings have access to the park. But members of two private clubs—the Players Club and the National Arts Club—and guests of the exclusive Gramercy Park Hotel can also gain entry.

To find out more about things to do, see, eat and drink in Manhattan, and discover other neighborhoods in the area, visit our Manhattan borough guide.

Map of Gramercy and Flatiron and travel information

The combined Gramercy and Flatiron neighborhoods lie east of Chelsea, running north from E 14th St to E 30th St between Fifth Ave and the East River (minus the chunk from 23rd St to 30th St between Lexington Ave and the river, known as Kips Bay). However, as with many NYC neighborhoods, the borders are disputed and evolving—NoMad is slowly catching on as the new name for the blocks north of Madison Square Park.

The area is served by the nexus of subway lines (L, N, Q, R, 4, 5, 6) that converge at 14th St–Union Sq station, offering a direct link to lower Manhattan, the Upper East Side, Brooklyn, Queens and the Bronx; there are further stops for the N, R and 6 at 23rd St and 28th St.

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Attractions in Gramercy and Flatiron

Flatiron Building

RECOMMENDED: 50 best New York attractions This 21-story Beaux Arts edifice once dominated midtown. Although it’s now dwarfed by other structures, when it debuted in 1902, the triangle-shaped monolith represented the threat and the thrill of modernity: Naysayers claimed it would never withstand the high winds plaguing 23rd Street, while revered photographer Alfred Stieglitz—who captured it in an iconic shot in 1903—wrote that it was “a picture of a new America still in the making.” Today, it’s possibly the least tourist-friendly New York landmark. The space above the ground-floor shops, occupied by publishing house Macmillan, is inaccessible to the public, but during office hours you can admire black-and-white photos and read a few panels on the history of the tower in its lobby. If you want to see the “point” offices (just over six feet wide at their narrowest), we suggest getting to work on the Great American Novel.

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Gramercy & Flatiron

Madison Square Park

Critics' pick

This public space was a highly desirable address when it opened in 1847, and is now a verdant oasis. It hosts a series of summer concerts, including the incredibly popular Mad. Sq. Kids series, which features some of the hottest bands in kids' music. The destination is also home to Shake Shack, a summer favorite (as evidenced by the shockingly long lines) for burgers, fries and, of course, shakes.

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Museum of Sex (MoSex)

RECOMMENDED: Museum of Sex (MoSex) Situated in the former Tenderloin district, which bumped-and-grinded with dance halls and brothels in the 1800s, MoSex explores the subject within a cultural context—but that doesn’t mean some content won’t shock the more buttoned-up visitor. On the ground floor, “Action!,” which screens around 220 clips from more than 150 years of sex on film, includes explicit scenes from such (literally) seminal porn flicks as Deep Throat. Upstairs, highlights of the permanent collection range from the tastefully erotic to the outlandish. Cop a feel of one of the silicone Real Doll torsos. An 1890s anti-onanism device could be confused with the S&M gear, which includes a nine-foot steel-framed love pen donated by a local dominatrix. Also of note are the Depression-era Tijuana Bibles—raunchy comic strips showing well-known characters like Donald Duck as you’ve never seen them before—and sex machines created by keen DIYers, such as the “Monkey Rocker,” constructed from a dildo and excercise equipment (it inspired the device in the Coen brothers’ Burn After Reading). The spacious gift shop is stocked with books and arty sex toys, and aphrodisiac elixers are served in a new café.

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Union Square

Critics' pick

RECOMMENDED: 50 best New York attractions This park is named after neither the Union of the Civil War nor the labor rallies that once took place here, but simply for the union of Broadway and Bowery Lane (now Fourth Avenue). Even so, it does have its radical roots: From the 1920s until the early ’60s, it was a favorite spot for tub-thumping political oratory. Following 9/11, the park became a focal point for the city’s outpouring of grief. These days you'll find the lively Greenmarket in warmer months, holiday shops in the winter and a summer concert series for kids.

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