Over the years, notable residents of Gramercy's townhouses have included President Theodore Roosevelt, actor James Cagney, and scribes O. Henry, Oscar Wilde and Eugene O'Neill. In many ways, the neighborhood hasn't changed much since they left. Its center, Gramercy Park, is a remnant of a bygone era—it's a private oasis, a giant backyard for area residents' exclusive enjoyment. (There's only one other private park in New York City—at Sunnyside Gardens in Queens). The green space looks much the same as it did in the 19th century, and usually visitors must content themselves to peek through the fence at its lush greenery and impeccable landscaping. There are exceptions, however: Gramercy Park opens to the public every year for Christmas Eve caroling, and those willing to shell out for a night at the Gramercy Park Hotel receive the same access as those who pay an annual fee for a key to the park. The surrounding streets, meanwhile, have remained more or less continuously fashionable for 180 years—they're packed with notable architecture; diverse dining options like Casa Mono and Friend of a Farmer; and nightlife—especially live music at Irving Plaza, The Gramercy Theatre and Jazz Standard. We bet President Roosevelt would be delighted to live there even today.
Landmarks Around the Park
A quick stroll around Gramercy Park's vicinity yields peeks at landmarks that are notable both for their architecture and for what goes on inside. The National Arts Club is worth a look for its facade alone—remodeled in the 1880s by Calvert Vaux, the building's exterior features busts of Shakespeare, Goethe, Dante and others, along with a carving of Michelangelo's head. Inside, some gallery shows and other events are open to the public. And if you find a member who'll bring you to the dining room as a guest, the cuisine will be well worth the effort. The Players, another private club, has counted the likes of Mark Twain, Norman Rockwell and Arthur Miller among its ranks. Its home, a Stanford White–remodeled mansion, mostly hosts private events for the organization's illustrious membership, but occasionally opens its doors to the public for special events. The Brotherhood Synagogue inhabits a former Quaker meetinghouse distinguished by, among other features, its soaring windows and distinctive pediment. Today, the Greek Revival building hosts a full slate of community activities including, for example, concerts and yoga. Another house of worship, The Parish of Calvary–St. George's, is a national landmark and a striking Romanesque Revival structure. And at Stuyvesant Square, a four-acre public park (no key required!), you can salute Gertrude Vanderbilt Whitney's bronze statue of Peter Stuyvesant himself (his great-great grandson sold the land to the City for the princely sum of $5 in 1836).
Rock Music Venues: Irving Plaza and The Gramercy Theatre
17 Irving Place and 127 E. 23rd St.; 212-777-6800
Historic concert hall Irving Plaza has a spot-on replica of the original marquee and plenty of cool acts gracing its stage. The ballroom has hosted a miles-long cavalcade of rock legends, including a split bill between The Strokes and The White Stripes at the height of the garage-rock craze; Green Day performing American Idiot in its entirety back when it was a concept album and not a Broadway show; and a surprise performance from Paul McCartney. The Gramercy Theatre, after previous incarnations as a movie house and an Off-Broadway theater, started hosting rock shows in 2007—about 70 years after it first opened. The 600-capacity room hosts big names such as Gary Numan and even the occasional comedy show by the likes of Charlene Yi. Taken together, the two venues make Gramercy a dark-horse candidate for rockin'-est NYC neighborhood.
Gramercy shopping embraces the classic, the lightly used and the timeless. Thrift and consignment shops thrive in the area. Vintage Thrift stocks clothes, housewares, furniture and what its proprietors call “tchotchkes.” Sales benefit the United Jewish Council of the Lower East Side. The City Opera Thrift Shop, meanwhile, might surprise you with the likes of a Hardman baby grand piano. Housing Works Thrift Shop sells a wide variety of used clothing, housewares, books, art and—a particular favorite with its customers—furniture. The store's larger mission is to support the well-being of men and women with AIDS.
Gramercy Park Hotel
2 Lexington Ave., 212-920-3300
Stay at the Gramercy Park Hotel, and you'll receive what may just be the neighborhood's best perk: access to Gramercy Park itself. No more wandering around the park's perimeter, peeking inside—you'll be able to enjoy the grounds like a local. Inside the hotel, the smell of crackling pine lends the premises a rustic warmth. Even if you're not staying at the Gramercy Park Hotel, the site offers plenty for you to relish. Its Rose Bar and Jade Bar require reservations after 10pm (requests are taken via email only). During that time, you can sip pricey cocktails and feast your eyes on art by Keith Haring and Richard Prince and a rare collaboration between Andy Warhol and Jean-Michel Basquiat. Or perhaps you'll be more interested in gawking at the likes of Leonardo DiCaprio, the cast of Entourage and the countless other glitterati who frequent the place. Finally, the hotel's on-site restaurant, Maialino, dishes out cuisine from the esteemed Danny Meyer, and his fare lives up to the hype. Foodies often laud such dishes as the malfatti al maialino (pasta with suckling pig ragù) with a fervor bordering on fanaticism.
129 E. 18th St., 212-473-7676
It's the oldest continually operating bar in New York City—having survived Prohibition by operating as a “flower shop,” with patrons gaining entry through a secret knock on a phony fridge door. O. Henry famously wrote The Gift of the Magi from a booth in its front room, whose walls are plastered with pictures of celebrities singing its praises. But Pete's Tavern is first and foremost a down-to-earth watering hole with friendly service, solid pub food and a great beer selection. (Try Pete's own 1864 Original Ale, named for the year in which Pete's opened.) Stop by to take in a piece of New York history (the rosewood bar and dining booths are original); the place is typically dominated by the regulars, most of whom seem as if they've known the chatty bartenders for years. Monday evening is a great time to sample the cuisine. That night, $13.95 will get you a salad, a bowl of pasta and a glass of wine or beer.
138 E. 27th St., 212-889-2850
Repertorio Español, an esteemed venue for Spanish-language performances, remains one of the few repertory theater companies in the City, with a constantly rotating repertoire of 15 plays. “You can come almost every day of the week and see a different play,” says associate producer José Antonio Cruz. Want to know what's playing today? Find the current schedule here. If you're looking for a bargain, try scoring tickets to the 2:30pm performance on the last Sunday of each month, when the second in a pair of tickets costs just a dollar. And don't fret if you haven't breathed a word of Spanish since high school; for just $3 you can rent an earpiece for real-time English translation and enjoy the show like a native Spanish speaker.
116 E. 27th St., 212-576-2232
Facing tough competition in a city long recognized as an international jazz destination, Jazz Standard has nevertheless carved out its own niche since hitting the scene in 2002. In fact, the Mingus Big Band—a frequent performer at the venue—won the 2011 Grammy Award for Best Large Jazz Ensemble Album for a live CD they recorded there. The venue is located beneath Blue Smoke, and patrons can order from the restaurant's full menu of mouthwatering barbecue and tasty signature drinks (though there's no drink minimum, you'll be hard-pressed to resist a mint julep or two to wash down your pulled pork and collard greens) while listening to swingin' tunes. And the music den's appeal stretches beyond its headline performers. If you're looking to nurture your children's inner Satchmo, for example, you can take them to Jazz for Kids—a weekly performance by an all-kids (ages 6 to 16) jazz band—on Sundays at 1pm. For a suggested donation of just $5, kids can watch their peers bring on the funk and, if inspired by what they see, even audition for their own spot in the band.
Theodore Roosevelt Birthplace
28 E. 20th St., 212-260-1616
When thinking about presidential birthplaces, the image of a rural log cabin probably comes to mind more readily than a Manhattan town house. However, Theodore Roosevelt, in fact, hails from New York City (the only US president to boast an NYC upbringing), and his family's brownstone—where, as an ailing boy, Teddy lived a decidedly unglamorous Manhattan childhood—is open to the public for free guided tours. (Well, an approximation of his brownstone, anyway—this re-creation was built a few years after the original was torn down.) History buffs should arrive early to explore the ground-floor gallery prior to their tour, but, if the momentous artifacts inside—like the 50-page speech that saved Roosevelt from an assassination attempt or a rare photograph signed by Abraham Lincoln—cause you to miss it, another tour will start in an hour (the last one leaves at 4pm). When visiting the house's period rooms, be sure to ask your guide about the master-bedroom furniture set, which was purchased for an extravagant $3,000 in 1865. Call ahead before you go, as the home has been undergoing numerous renovations over the past few yeras.
W New York – Union Square
201 Park Ave. South, 212-253-9119
Located just outside of Gramercy proper, the W Hotel is, quite literally, steps away from the neighborhood. Housed in the beaux-arts Guardian Life Building, which turns a century old in 2011, the hotel is one of the area's most distinctive landmarks. The W calls its different room classes “Wonderful,” “Spectacular” and “Mega” (to go along with suite names including “Fantastic,” “Wow” and, naturally, “Extreme Wow”)—and while at first glance these monikers may seem a bit grandiose, most patrons will confirm that the lodging lives up to its billing; even an amenity as standard as the bed delivers an extraordinary experience here, as guests consistently rave about the W's preternaturally comfortable mattresses. Outside the rooms, the W's concierges are a tremendous resource for the discerning guest. They're eager to share their knowledge of the neighborhood and the City.
Gramercy is home to a far-reaching array of restaurants equipped to satisfy every palate. Mario Batali's cozy Casa Mono dispenses tapas like sweetbreads, duck egg and quail. Choshi dishes up outstanding sushi at reasonable prices in a casual setting suitable for a quick stopover with friends or a low-key date. Friend of a Farmer has long been regarded as one of the premier places in NYC to enjoy a satisfying brunch, and Gramercy Tavern offers seasonal New American cuisine, attentive service and refined surroundings that make it one of the City's best-known fine-dining establishments. Go with the tasting menu and you'll be treated to what seem like endless waves of delicious, imaginative fare composed of greenmarket ingredients. Finally, if you're after a top-notch cup of joe, 71 Irving Place is run by coffee nerds who roast their own beans in a Hudson Valley facility. Its lineup of quality coffees includes the ever-popular iced Sinful Delight, flavored with caramel, chocolate and nuts.
Spin New York
48 E. 23rd St., 212-982-8802
Seasoned pros mingle with regular joes at this trendy table tennis lounge, which boasts a liquor license, an on-site restaurant, 17 tables, Olympic-quality flooring and a center court flanked by stadium-style bleachers. The venue also accepts reservations from those who'd rather not wait for a table. Every Friday, SPiN hosts 12 of the nation's top players in an event with $500 at stake. And on Monday nights, open tournaments give non-pros a chance to win a month of free court time. But don't despair if you're not a champ; you can still save cash on individual visits by purchasing a membership.