6 p.m. An earlier dinner
To make the most of the UWS, you’re looking at a full night ahead of you, and we recommend getting in an earlier dinner to kick off. In case you skipped Italian for lunch, head to Bosino on 103rd. Located in a charming alcove with al fresco dining in the warmer months, the restaurant pairs its authentic Sicilian pasta dishes with almost familial service. Menu highlights include the classic lasagna, mushroom cream tortellini, and margherita pizza, though you’d be remiss to not ask to hear the night’s specials, which in prior nights have included show stoppers like a braised short rib ravioli. Should you find yourself in the mood for a different type of noodle, Jin Ramen on 82nd and Amsterdam serves a great bowl of tonkotsu. For a blend of East and West, Flor de Mayo combines Chinese and Peruvian cuisines. A sublime dinner bounces between the two, with yucca, squid fried rice, and lomo saltado all finding a place at the table. Georgian food at Chama Mama is another great option—first timers will do well to order the Taste of Georgia platter for a smattering of dips, veggies, housemade bread, and Georgian smoked cheese. The Adjaruli Khachapuri is another crowd favorite with made-to-be-captured cheese pulls. Our last option (though really, the neighborhood is teeming with great restaurants): Sushi W, where you can enjoy reasonably-priced omakase and an optional sake pairing in a cozy, romantic setting.
7 p.m. Sneaking in a sweet treat
If you held off on seeing a dessert menu at dinner, that actually might’ve been for the best as locals know you’re not without—perhaps even better—options elsewhere. The newly opened Softside counter delivers delightful summery bites in the form of soft serve sugar cones. They have four basic flavors: vanilla, chocolate, strawberry, and pistachio, but we recommend mixing it up with one of their sundaes like the Riff made with honey, olive oil, and sea salt, or their brûléed banana split. Rather sink your teeth in something warm and gooey? Enter one of the city’s most famous bakeries: Levain. Their cookies resemble little mountains stratified with layers of buttery dough and melty chocolate chips. They’re big cookies for the Big Apple. Janie’s is another tasty option—order at least one pie crust cookie!—tucked away downstairs on 80th Street between Broadway and Amsterdam.
You’re nearly drowning in ice cream options around here, but one of our favorites is Salt & Straw, the West Coast gem that finally made its way to NYC last year, opening a location in the Upper West Side and another in the West Village. Flavors often riff on the classics in unexpected ways—in the fall, for example, order Apple and Cheddar Cinnamon Rolls or Pear and Blue Cheese (the less adventurous might opt for the Salted, Malted, Chocolate Chip Cookie Dough).
8 p.m. Evening entertainment
While the white glove scene at Lincoln Center adds some extravagance to a night out (dress up for a night at the opera, ballet, or New York Philharmonic), crawling the neighborhood’s jazz bars is a fantastic way to see live performances in a way that’s a little more low-key. Steps off of Lincoln Center, Dizzy’s Club serenades its crowds over views of the Manhattan skyline and a rotating menu of seasonal bites. Farther up between 105th and 106th, Smoke Jazz & Supper Club is just the place to stop by for dinner and show. It’s all exposed brick, moody red curtains, and a baby grand on stage here. Regular programming includes jazz, blues, and Latin music, and soft lighting makes friends out of the shadows. Or, look ahead to see who’s playing at the Beacon—it’s a popular tour spot for comedians and musicians.
10 p.m. Sips and tipples
Some may hold the misconception that the Upper West Side is one of the rare New York neighborhoods that does indeed head to bed after sundown, and there’s no better way to bust the myth than visiting our storied bars. Dive Bar down on 96th purports to have “beer as cold as your ex’s heart,” a steal with some brews going as low as $5 a pint. As its, well, everything suggests, Dive Bar welcomes all those looking to let their hair down and go in on some buffalo wings or nachos. Fret not if you’re hoping to grab a few more photos in your night out best, Nobody Told Me serves sophisticated light bites like oysters on the half shell and buttoned-up cocktails like the vodka and elderflower-forward Morningside—a nightcap worth dressing up for. (It’s an especially great option if you’ve just dined at Sushi W given the proximity.) Stop in at Tiki Chick for a frozen drink (and if you get hungry, one of the best cheap eats you’ll find in the $5 fried chicken sandwich), then head next door to E’s for a beer, spicy margarita, and board games.
Where to stay
The Upper West Side is largely residential, so we recommend staying nearby instead—check out our list of the best Midtown Manhattan hotels, or head just across the park to the iconic Carlyle, The Mark, or The Surrey.
Madison Flager
Associate commerce director
Madison Flager is the Associate Commerce Director at Condé Nast Traveler, where she oversees travel booking and shopping content. She called the Upper West Side home for six years before moving (slightly) north to Harlem.
Kat Chen
Kat Chen is the editorial assistant at Condé Nast Traveler where she works on Destination Guides content. She lived in the UWS for the past five years before making the leap over the Hudson River to Jersey.