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Union Square | Flatiron District | Gramercy Park

Updated by Jacinta O’Halloran

Union Square is a hub of seemingly never-ending activity and people-watching, a distinction amplified by the bordering quieter neighborhoods of Gramercy and the Flatiron District. When that certain brand of New Yorker says they don’t like to travel above 14th Street, they’re usually thinking about Union Square as the cutoff.

Making the Most of Your Time

Union Square seems like it’s busy at just about every time of day and night, with people hanging out on the steps, eating lunch, or watching street performers, but market days—Monday, Wednesday, Friday, and Saturday—are even busier. Early weekday mornings are quietest, before the market is set up, though without all the people, the area loses some of its allure.

This is definitely an area for strolling, shopping, and eating, so plan your visit around a meal—or several.

If you’re planning to eat at the Shake Shack in Madison Square Park, come before noon to avoid long lines.

Coffee and Quick Bites

Eataly.
There are multiple restaurants, take-out shops, a Nutella bar, and cafés, as well as a rooftop brewery at Mario Batali’s Italian food emporium. You can also shop for gourmet Italian chocolates, coffees, gelati, and pastries. | 200 5th Ave., at 23rd St. , Flatiron District | 212/229–2560 | www.eataly.com | Station: N, R to 23rd St.

Irving Farm Coffee Roasters.
Steps from Union Square, this busy little café (known to locals as 71 Irving) roasts its own beans—always a good sign—and serves good people-watching along with sandwiches, muffins, and snacks. | 71 Irving Pl. , Union Square | 212/995–5252 | www.irvingfarm.com | Station: 4, 5, 6, L, N, Q, R to 14th St.–Union Sq.

Think Coffee.
Maybe you like a little social and environmental awareness with your caffeine, or perhaps the cold-brewed iced coffees, Spanish lattes, and cool playlist are sufficient. | 123 4th Ave., between 12th and 13th Sts. , Union Square | 212/614–6644 | www.thinkcoffee.com | Station: 4, 5, 6, L, N, Q, R to 14th St.–Union Sq.

Top Experiences

Strolling in Union Square Park and checking out the produce and other goodies at the greenmarket

Browsing the miles of books in the Strand bookstore

Strolling from Irving Place to Gramercy Park, and around the perimeter of this historic, private park

Getting Here and Around

Union Square is a major subway hub, with the 4, 5, 6, L, N, Q, and R lines all converging here. For Madison Square Park and the Flatiron District, take the N or R train to 23rd Street (this lets you out on Broadway). The 6 stops at 23rd and 28th Streets (on Park Avenue South).

Seasonal Highlights

Union Square Holiday Market. From Thanksgiving to Christmas, this outdoor market has more than 150 vendors selling unique, often locally made products. | www.urbanspacenyc.com

Madison Square Eats. This monthlong pop-up food market happens twice a year (spring and fall) across the street from Madison Square Park, and includes popular vendors like the Red Hook Lobster Pound, Fire Belly Korean BBQ, and Roberta’s Pizza. | www.madisonsquarepark.org/mad-sq-eats.

Union Square

The energy of Union Square reaches its peak during greenmarket days (Monday, Wednesday, Friday, and Saturday), when more than 140 regional farmers and food purveyors set up shop on the square’s north and west sides to peddle everything from produce to meat and fresh fish to baked goods. The market is a great place to rub elbows with—and get elbowed by—local shoppers and chefs, and a great source for tasty souvenirs (locally produced honeys, jams, pickles, and cheeses) as well as lunch. Find a bench in the park to savor your goodies and take in the scene. Political rallies sometimes happen here, too.

Even on a nonmarket day, Union Square regularly has vendors of all kinds, selling everything from art to jewelry to T-shirts. New York University students, nannies with their charges, visitors, and other locals gather in this open space that can at times feel more like an outdoor version of Grand Central Terminal than a park. Just south of Union Square, on Broadway at 12th Street, is the Strand, a giant bookstore that attracts book lovers like a magnet.

Union Square Park and Greenmarket.
A park, farmers’ market, meeting place, and the site of rallies and demonstrations, this pocket of green space sits in the center of a bustling residential and commercial neighborhood. The name “Union” originally signified that two main roads—Broadway and 4th Avenue—crossed here. It took on a different meaning in the late 19th and early 20th centuries, when the square became a rallying spot for labor protests; many unions, as well as fringe political parties, moved their headquarters nearby.

Union Square is at its best on Monday, Wednesday, Friday, and Saturday (8–6), when the largest of the city’s greenmarkets gathers farmers and food purveyors from the tristate area. Browse the stands of fruit and vegetables, flowers, plants, fresh-baked pies and breads, cheeses, cider, New York State wines, fish, and meat. Between Thanksgiving and Christmas, there is a popular market where artisans sell gift items and food in candy-cane-stripe booths toward the square’s southwest end.

New York University dormitories, theaters, and cavernous commercial spaces occupy the handsomely restored 19th-century commercial buildings that surround the park, along with chain coffee shops and restaurants. The run of diverse architectural styles on the Decker Building at 33 Union Square West is as imaginative as its former contents: this was once home to Andy Warhol’s studio. The building at 17th Street and Union Square East, now housing the New York Film Academy and the Union Square Theater, was the final home of Tammany Hall, an organization famous in its day as a corrupt and powerful political machine. Statues in the park include those of George Washington, Abraham Lincoln, Mahatma Gandhi (often wreathed in flowers), and the Marquis de Lafayette (sculpted by Frederic Auguste Bartholdi, designer of the Statue of Liberty). Plaques in the sidewalk on the southeast and southwest sides chronicle the park’s history from the 1600s to 1800s. After years of legal battles, the once-crumbling pavilion in the northern end of the park was reincarnated in summer 2014 as an upscale, seasonal restaurant: The Pavilion. The restaurant provides alfresco dining (from April to October) with ingredients sourced from the surrounding greenmarket. | From 14th to 17th St., between Broadway and Park Ave. S , Union Square | Station: 4, 5, 6, L, N, Q, R to 14th St.–Union Sq.

Flatiron District

The Flatiron District—anchored by Madison Square Park on the north and Union Square to the south—is one of the city’s busiest neighborhoods, particularly along 5th Avenue and Park Avenue South. Once known as Ladies’ Mile because of the fashionable row of department stores where women routinely shopped, the area is still a favorite for lady-spotting because of the number of modeling agencies and photography studios here. Lovely Madison Square Park, a pleasant green space hemmed in by the neighborhood’s notable architecture—from the triangular Flatiron to the dazzling, gold-pyramid-topped New York Life Building and Metropolitan Life Tower, with its elegant clock face—is the best place to savor the view. Sit and admire the scene with a burger and shake from the park’s always-busy Shake Shack, or takeout from the mother (or “mamma mia”) of all Italian markets, Eataly, across the street from the west side of the park.

Top Attractions

Flatiron Building.
When completed in 1902, the Fuller Building, as it was originally known, caused a sensation. Architect Daniel Burnham made ingenious use of the triangular wedge of land at 23rd Street, 5th Avenue, and Broadway, employing a revolutionary steel frame that allowed for the building’s 22-story, 286-foot height. Covered with a limestone-and-white-terra-cotta facade in the Italian Renaissance style, the building’s shape resembled a clothing iron, hence its nickname. When it became apparent that the building generated strong winds, gawkers would loiter at 23rd Street hoping to catch sight of ladies’ billowing skirts. Local traffic cops had to shoo away the male peepers—one purported origin of the phrase “23 skidoo.” There is a small display of historic building and area photos in the lobby, but otherwise you have to settle for appreciating this building from the outside, at least for now; the building may be converted to a luxury hotel when current occupant leases expire in late 2018. | 175 5th Ave., bordered by 22nd and 23rd Sts., 5th Ave., and Broadway , Flatiron District | Station: N, R to 23rd St.

Madison Square Park.
The benches of this elegant tree-filled park afford great views of some of the city’s oldest and most charming skyscrapers—the Flatiron Building, the Metropolitan Life Insurance Tower, the gold-crowned New York Life Insurance Building, and the Empire State Building—and serve as a perfect vantage point for people-, pigeon-, and dog-watching. Add free Wi-Fi, the newly renovated Shake Shack, temporary art exhibits, and free summer and fall concerts, and you realize that a bench here is definitely the place to be. New York City’s first baseball games were played in this 7-acre park in 1845 (though New Jerseyans are quick to point out that the game was actually invented across the river in Hoboken, New Jersey). On the north end of the park, an imposing 1881 statue by Augustus Saint-Gaudens memorializes Civil War naval hero Admiral David Farragut. An 1876 statue of Secretary of State William Henry Seward (the Seward of the term “Seward’s Folly,” coined when the United States purchased Alaska from the Russian Empire in 1867) sits in the park’s southwest corner, though it’s rumored that the sculptor placed a reproduction of the statesman’s head on a statue of Abraham Lincoln’s body. | From 23rd to 26th St., between 5th and Madison Aves. , Flatiron District | 212/520–7600 | www.madisonsquarepark.org | Station: N, R to 23rd St.

Worth Noting

Appellate Division Courthouse.
Sculpted by Frederick Ruckstull, figures representing Wisdom and Force flank the main portal of this imposing Beaux Arts courthouse, built in 1899. Melding the structure’s purpose with artistic symbolism, statues of great lawmakers line the roof balustrade, including Moses, Justinian, and Confucius. In total, sculptures by 16 artists adorn the ornate building, a showcase of themes relating to the law. This is one of the most important appellate courts in the country: it hears more than 3,000 appeals and 6,000 motions a year, and also admits approximately 3,000 new attorneys to the bar each year. Inside the courtroom is a stunning stained-glass dome set into a gilt ceiling. The main hall and the courtroom are open to visitors weekdays from 9 to 5. All sessions, which are generally held Tuesday to Thursday at 2 pm, are open to the public (visitors can call the main number ahead of time to be sure court is in session). | 27 Madison Ave., entrance on 25th St. , Flatiron District | 212/340–0422 | www.courts.state.ny.us/courts/ad1 | Weekdays 9–5 | Station: N, R, 6 to 23rd St.

Metropolitan Life Insurance Company Tower.
When it was added to the original building on this site in 1909, the 700-foot tower resembling the campanile of St. Mark’s in Venice made this 1893 building the world’s tallest; it was surpassed in height a few years later (by the Woolworth Building). It was stripped of much of its classical detail during renovations in the early 1960s, but remains a prominent feature of the Midtown skyline today. The clock’s four faces are each three stories high, and their minute hands weigh half a ton each. If the view from the park doesn’t quite cut it, you can now reserve a room in the skyline itself: in 2015, Marriott International and Ian Schrager opened a 273-room luxury hotel, the New York Edition Hotel, in the long-vacant clock-tower portion of the building. | 1 Madison Ave., between 23rd and 24th Sts. , Flatiron District | Station: N, R, 6 to 23rd St.

Museum of Mathematics (MoMath ).
There’s no exact formula to get kids excited about math, but the sleek, two-floor Museum of Mathematics (MoMath)—the only cultural institution devoted to math in all of North America—comes close to finding the perfect fun-to-math ratio. Kids can ride square-wheel trikes, create human fractal trees, build virtual 3-D geometric shapes (which can be printed out on a 3-D printer for a fee), use lasers to explore cross sections of objects, solve dozens of puzzles, and generally bend their minds while they unknowingly multiply brain cells (sshh!). MoMath’s newest exhibition, Robot Swarm, allows kids to explore swarm robotics and interact with two dozen small (Roomba-like), glowing robots, using simple math rules. Exhibits are best suited to kids ages six and up, but preschoolers can still enjoy many of the interactive exhibits, like the Math Square, a light-up floor programmed with math games, simulations, and patterns. TIP The museum closes at 2:30 pm the first Wednesday of every month. Save $1 by ordering tickets in advance online. | 11 E. 26th St., between 5th and Madison Aves. , Flatiron District | 212/542–0566 | www.momath.org | $16 | Daily 10–5 | Station: N, R to 28th St.

Museum of Sex.
Ponder the profound history and cultural significance of sex at this 14,000-square-foot museum while staring at vintage pornographic photos, S&M paraphernalia, antimasturbation devices from the 1800s, explicit film clips, vintage condom tins, and a collection of artwork. The Spotlight on the Permanent Collection gallery features revolving artifacts and ephemera, as well as a “Jump for Joy” bounce house (of inflated breasts) that was originally part of a recent exhibition, Funland: Pleasures & Perils of the Erotic Fairground. Other recent exhibits have probed such topics as desire on the Internet and the sex lives of animals, as well as a translation of the campground setting as a surreal adult playground, complete with tents, campfire, and park rangers. The subject matter is given serious curatorial treatment, though the gift shop is full of fun sexual kitsch. Only patrons over 18 are admitted. TIP After visiting the museum’s exhibitions, sate your appetite with a kinky cocktail or gourmet coffee and pastry in the museum’s Play bar and Nice & Sweet café. | 233 5th Ave. | New York | 212/689–6337 | www.museumofsex.com | $17.50 | Sun.–Thurs. 10–9, Fri. and Sat. 11–11 | Station: N, R to 28th St.

Gramercy Park

The haste and hullabaloo of the city calms considerably in the residential neighborhood of Gramercy Park. Dignified Gramercy Park, named for its 1831 gated garden ringed by historic buildings and private clubs, is an early example of the city’s best creative urban planning. Just north of the park is Ian Schrager’s reincarnation of the Gramercy Park Hotel on Lexington Avenue. South of the park, running north to south from 14th Street, is Irving Place, a short street honoring Washington Irving, which feels calm, green, exclusive, and has a combination of old and new eateries, stores, and architecture. Pete’s Tavern, on Irving Place since 1864, maintains its claim as the oldest original bar in the city. Two famous writers, O. Henry (Gift of the Magi ) and Ludwig Bemelmans (Madeline ), were “inspired” here, probably by the amazing eggnog or Pete’s House Ale.

Gramercy Park.
You may not be able to enter this private park (the only truly private park in Manhattan—only those residing around it have keys), but a look through the bars in the wrought-iron fence that encloses it is worth your time, as is a stroll around its perimeter. The beautifully planted 2-acre park, designed by developer Samuel B. Ruggles, dates from 1831, and is flanked by grand examples of early-19th-century architecture and permeated with the character of its many celebrated occupants.

When Ruggles bought the property, it was known as Krom Moerasje (“little crooked swamp”), named by the Dutch settlers. He drained the swamp and set aside 42 lots for a park to be accessible exclusively to those who bought the surrounding lots in his planned London-style residential square. The park is still owned by residents of the buildings surrounding the square, although neighbors from the area can now buy visiting privileges. Guests of the Gramercy Park Hotel also enjoy coveted access to this private park. In 1966 the New York City Landmarks Preservation Commission designated Gramercy Park a historic district. Notable buildings include No. 15, a Gothic Revival brownstone with black granite trim designed by Calvert Vaux, which was once home to Samuel Tilden, governor of New York. A secret passageway to 19th Street permitted Tilden to evade his political enemies. It is now home to the 100-year-old National Arts Club. Next door at No. 16 Gramercy Park South lived the actor Edwin Booth, perhaps most famous for being the brother of Lincoln’s assassin. In 1888 he turned his Gothic-trim home into the Players Club, a clubhouse for actors and theatrical types who were not welcome in regular society. A bronze statue of Edwin Booth as Hamlet has pride of place inside the park. TIP Alexander Calder’s iconic, monumental outdoor sculpture Janey Waney (1969) is installed inside the park and can be viewed through the railings. | Lexington Ave. and 21st St. | New York | Station: 4, 5, 6, L, N, Q, R to 14th St.–Union Sq.; 6 to 23rd St.

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