The 20 coolest things to do uptown

Despite creating the whole street-art phenomenon, NYC isn’t particularly friendly to taggers. Luckily, there are still a few nooks, like this spray-paint staple at the Jackie Robinson Educational Complex playground, where artists have been encouraged to do their thing since the late ’70s.

Visitors may think they know this venerable theater from TV’s Showtime at the Apollo. But as the saying goes, the small screen adds ten pounds: The city’s home of R&B and soul is actually quite cozy. Known for helping to launch the careers of Ella Fitzgerald, James Brown and D’Angelo, among others, the Apollo continues to mix veteran talents with younger artists such as Lykke Li and Pharrell.

The Upper East Side added to its craft-beer roster with the Jeffrey (from the team behind LIC’s celebrated Alewife). Enter through the café-bar’s right-hand door and sit along the slender wood-and-copper bar for a view of 30 taps and the Queensboro Bridge. Select from the New York State–centric suds list, confident that the pour will be the optimal temperature and pressure, thanks to a custom draft system, and, you know, get drinking, dude.

It’s so lovely and bucolic here that you might just forget you’re in Manhattan. Set in a splendid park overlooking the Hudson River, the Cloisters houses the Met’s medieval art and architecture collections. A path winds through the peaceful grounds to a castle that seems to have survived from the Middle Ages. Be sure to check out the famous Unicorn Tapestries, the 12th-century Fuentidueña Chapel and the Annunciation Triptych by Robert Campin.

Head to this arts venue to enjoy alt-cool programming, like the Uptown Showdown—in which teams of comics square off in ridiculous debates on crucial topics (e.g., Dogs or cats? Discuss.)—and the Thalia Docs indie-film series.

Resplendently restored, this spacious former vaudeville theater hosts a variety of touring staples (your ZZ Tops, your Pettys) and younger bands to keep the, erm, youngsters happy (the National, Tegan and Sara). While the vastness can be daunting to performers and audience alike, the baroque, gilded interior and uptown location make you feel as though you’re having a real night out on the town.

The soul-food restaurant was a hit before serving its first dish a few years back—the promise of star chef Marcus Samuelsson (Aquavit), down-home eats from across the globe and energetic jazz bands stirred up plenty of hype. Rave reviews followed. And Red Rooster totally delivered.

No matter which wing you wander through or where your curiosities lie (dinosaurs, gems or something else entirely), it’s hard to explore this Upper West Side fixture without being awestruck. There’s the rotunda’s hulking Barosaurus skeleton replica, the fighting squid and whale (from, yes, Noah Baumbach’s The Squid and the Whale), Neanderthals and the spectacular $210 million Rose Center for Earth and Space.

This place is huge. The NYC landmark houses a series of 16 period rooms from the late 19th century, designed by such luminaries as Louis Comfort Tiffany and the Herter Brothers. The Armory has been transformed into one of the city’s premier alternative spaces for showing art and performances (most recently, Kenneth Branagh’s bloody and brilliant Macbeth).

While the Upper West Side’s arts scene is often identified with the highbrow offerings at Lincoln Center, there are dick jokes aplenty just 14 blocks north. This club’s been kicking since the ’80s comedy boom, welcoming both open-mikers and established names.