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.
What is it? A well-realized gastropub–The Penrose is a crowd-pleaser.
Why we like it: Comfy, stylish–a bit of hip downtown, uptown.
Time Out tip: The Penrose does have a ton of seating but it still gets crowded on Saturday nights.
Address: 1590 2nd Avenue
Opening Hours: Monday - Friday, 11:30am-4am; Saturday & Sunday, 9:30am-4am
Expect to Pay: Cocktails are $15, Beers are about $8; Wine glasses are $13-ish, bottles are around $55, there’s also bottles of sparkling that reach up to $210. Small plates of food are about $12-$15 while a main can go for between $17-$34
What is it: One of NYC’s premier beer bars
Why we like it: Home to a 65-seat outdoor biergarten, a coffee shop, a mixology lab, The Jeffrey wants to be your go-to for whatever you’re into.
Time Out tip: This is a destination for beer nerds, yes. But it’s also the kind of place that, on a sunny weekend afternoon, you can bring the whole team and have a great time. It’s right under the Queensboro Bridge, so if you’re going at night and wanna sit outside, bring a jacket.
Address: 311 East 60th Street
Opening Hours: Monday - Wednesday, 4pm-midnight; Thursday - Saturday, noon-1am; Sunday, noon-midnight
Expect to pay: Beers range, depending but most are around $8. Cocktails average $15. Wine glasses are $15, bottles are $65. Small plates are mostly about $8, tacos are $7-ish per with a minimum of two to an order; big plates are from about $15 to $20.
What is it: A low-key Scottish pub with a huge scotch whiskey selection.
Why we like it: It’s not all about the price-tag on single-malt here; the collection is more thoughtfully curated than that.
Time Out tip: There are house rules you’d do well to observe: There’s no such thing as the best whiskey. There's a 5% discount for Tinder dates (with proof). Do NOT close your tab after each drink, you Gen Zers. Don’t ask for free drinks—it’s gauche and annoys bartenders. Fellas: respect women or get the boot.
Address: 1609 2nd Avenue
Opening Hours: Monday - Thursday, 5pm-2am; Friday & Saturday, 4pm-4am; Sunday, 4pm-midnight
Expect to pay: Cocktails are around $16, food is around $8, beer around $9, wine is at around $13/glass and $50/bottle. Whiskeys have a vast range, some hitting $150 for a pour.
What is it: An atmospheric, long-running lounge on a residential strip with no street-facing signage.
Why we like it: This place was a trailblazer in NYC and has maintained its intrinsic integrity through the years.
Time Out tip: There’s no storefront, so it may take you a minute to locate the entrance but trust us: it’s there. There’s no dress code, but keep it classy. Cash only.
Address: 300 East 89th Street
Opening Hours: Sunday - Thursday, 6pm-2am; Friday, 6pm-1am, Saturday, 6pm-4am
Expect to pay: House cocktails are $14, Beers are around $7, wine about $10/glass and bottles range wide from $30 to $100+. Food doesn’t break the bank, averaging $15.
Discover Time Out original video
