Gorgeous prewar apartments owned by blue-blooded socialites, soigné restaurants frequented by Botoxed ladies who lunch, the deluxe boutiques of international designers.… This is the clichéd image of the Upper East Side, and you’ll certainly see a lot of supporting evidence on Fifth, Madison and Park Avenues. Recently, however, pockets of downtown cool have migrated north, notably the growing food-and-drink enclave pioneered by Earl’s Beer and Cheese.
RECOMMENDED: Full guide of Manhattan, NY
Encouraged by the opening of Central Park in the late 1800s, affluent New Yorkers began building mansions along Fifth Avenue. By the start of the 20th century, even the superwealthy had warmed to the idea of giving up their large homes for smaller quarters, provided they were near the park, which resulted in the construction of many new apartment blocks and hotels. Working-class folk later settled around Second and Third Avenues, following construction of the defunct elevated East Side train line, but affluence remained the neighborhood’s dominant characteristic. Philanthropic gestures made by the moneyed classes over the past 130-odd years have helped to create the impressive cluster of art collections on Museum Mile—from 82nd to 105th Streets, Fifth Avenue is lined with more than half a dozen celebrated institutions, including theMetropolitan Museum of Art, the Solomon R. Guggenheim Museum and The Frick Collection.
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 the Upper East Side and travel information
Restaurants on the Upper East Side
Museums on the Upper East Side
Bars on the Upper East Side
The Penrose—named for a neighborhood in Cork, Ireland, where two of the owners grew up—brings a bit of the indie-chic East Village to Gossip Girl territory. Operated by the gastropub specialists behind the Wren and Wilfie & Nell, the joint would be run-of-the-mill farther downtown, where the trifecta of reclaimed wood, craft pours and pedigreed pub grub long ago joined the ranks of food-world clichés, but it’s a welcome change up here.
Tucked away on an aggressively average block in the doorman-less part of the Upper East Side, a set of red-velvet ropes leads to a heavy black door. The underground speakeasy seems like a seductive bachelor pad from the 1960s, where the attentive staff serves gussied-up drinks for the parties of overlapping limbs and fused-together faces.
The Alewife team opened this Upper East Side hangout. A custom draft system for the beer controls the pressure for optimal fizz. To pad the boozing, the chef will dole out elevated bar snacks, while keg pallets and lighting fixtures fashioned from plumbing parts decorate the space, including a 65-seat biergarten.
Choice acts keep New York’s most dapper nightspot on the map, while the steep cover charge and white-jacketed service makes sure riffraff doesn’t scuff up the bar’s most valued draw: original Ludwig Bemelmans murals. Not to be missed, spiffy (and pricey) cocktails preserve the bar’s classic character.
Shops on the Upper East Side
Discover Time Out original video