10 cool things to do in NYC after dark

Perched at the intersection of dinner theater and a party at Jay Gatsby’s house, this spectacular interactive performance is the sort of evening affair you’ll remember for the rest of your life. Gymnasts of Cirque du Soleil–like ability bend, flex and flow across the room; actors frolic from table to table, tapping selected visitors to go on special adventures in secret rooms; and dancers move elegantly and seductively across the room, all while you feast and imbibe to your heart’s content. It’s not cheap, but it’s definitely worth the money.

Diamond Horseshoe at the Paramount Hotel, 235 W 46th St; $140–$175, premium $275–$500

Considering the madness surrounding many New York attractions located along 42nd Street–Times Square, Grand Central and the U.N., it’s almost hard to believe there’s an oasis of holiday happiness along Manhattan’s greatest cross street. Yet Bryant Park’s holiday pop-up village hosts more than 125 boutique shops (perfect for knocking out some early holiday shopping), dozens of sit-down and to-go food options and a giant outdoor skating rink. If you have your own skates, bring ‘em; renting blades will cost you $15, but the rink itself is free. Best of all, you can browse and skate late—the village is open till midnight on Fridays and Saturdays and 10pm the rest of the week.

Bryant Park, between Fifth and Sixth Aves and 40th and 42nd Sts; free

Few New York tableaus are as iconic as Rock Center’s towering holiday tree—especially once the lights are flipped on. Sure, it may require braving the crowds of selfie stick-clutching tourists flowing out of Disneyfied Broadway shows on their way to the Top of the Rock, but gazing past the skating rink to the enormous pine covered in colorful points of brilliance, then looking higher to the surrounding skyscrapers…it’s enough to take even the most jaded native New Yorker’s breath away. Grab a coffee or cocoa, find a corner, and take in the beauty. Should that somehow grow old, you can always resort to the New Yorker’s go-to pastime: people-watching.

Rockefeller Plaza, between Fifth and Sixth Aves and 48th and 49th Sts; free

Model trains aren’t just toys for kids—at least, not if you present them the way the NYBG does at its after-hours train show. Grab a cocktail (or some spiked hot chocolate) and some tasty morsels, check out ice carvers and fire jugglers in action, then mosey on over to the Haupt Conservatory to see a quarter-mile of model trains running through hundreds of detailed models of NYC landmarks—all painstakingly made out of pieces of plants by artist Paul Busse. Plus, if you don’t feel like Uber-ing all the way to the north Bronx, you can ride up and back on an actual train—then finish out the night with a cocktail at the Campbell Apartment.

Bronx River Pkwy at Fordham Road; $35

Epic is a word tossed around far too casually, but it applies to the views from the top of NYC’s tallest building. Sure, the slog to the top is a little cheesy (stretch out your eye-rolling muscles before you hit the “See Forever” video presentation) but the views from the 100th floor observation deck make it worthwhile: The entire city (along with a huge chunk of New Jersey and Long Island) stretch in every direction, laid out like a shimmering carpet of light. But there’s a hack that’ll let you squeeze even more out of your pricey trip to the peak of New York—if you ask, the bartenders will serve your beers in plastic cups, allowing you to take in all 360 degrees of the view with a brew in hand.

One World Trade Center, West St at Vesey St; $32

Just because it’s cold and dark outside doesn’t mean you have to put away your bicycle. On the first Friday of every month, cyclists gather at Columbus Circle at 10pm for a fun, easy-going ride along the roads and bikeways of Central Park. You don’t have to have Tour de France dreams to participate; it’s a slow, easy ride, open to all bike riders, with guides at the ends of the pack to keep everyone safe. You don’t even need a light on your bike (technically, New York State mandates that any bike being ridden at night needs a headlight, but we won’t tell on you). With no cars and almost no pedestrian traffic, it’s almost like a ride through the countryside…except the country doesn’t offer views of midtown skyscrapers.

Columbus Circle, southwest corner of Central park at 59th Street; free

Between Netflix and the Cineplex, movie watching doesn’t have the same magic it used to. Unless you catch a film at this midtown theater, which puts even the Lincoln Square IMAX hall to shame. Built almost 50 years ago, the 1,131-seat cinema still maintains the luster of a lost age of movie viewing. Between the grand scale of its main hall, the elegant wooden trim and red carpeting, just walking into the theater feels every bit worth the price of admission—and that’s before the enormous screen lights up and the earth-shaking audio system is cranked. The latest James Bond flick, Spectre, is playing there starting November 5; trust us, there’s nothing like seeing Bond on a screen this big.

141 W 54th St; $15

Come Friday or Saturday night, most tourists have abandoned the Met for dinner or a show—which makes it the perfect time for locals to meander the halls of the nation’s largest art museum. If its scale and crowds normally put you off, this is your best chance to finally appreciate its wonders on your own time. Want to get a good look at Washington Crossing The Delaware? Hokusai’s The Great Wave off Kanagawa? Jasper Johns’s White Flag? The Temple of Dendur or the hall of Arms and Armor? They’re all yours for the viewing, as well as the rest of the more than two million items the Met has in its permanent collection. Besides, you’re a New Yorker. It’s not like you have to choose between going to the Met and going out—by the time it closes at 9pm, your night’s just getting started anyway.

1000 Fifth Avenue; $25 suggested admission

It doesn’t matter one iota what time the sun goes down when you’re at this celebrated cabaret room—because, as the name suggests, the stage and tables are all well underground. The talent performing on said stage, however, is anything but; some of the biggest names in the music and theater worlds have been known to grace it, from Patti LuPone to Jason Robert Brown to Tom Wopat. (Yes, that Tom Wopat.) Almost every seat offers a good view and good acoustics, the atmosphere is warm and inviting—and the food is actually pretty darn good, too. Plus, the schedule is jam-packed with talent all winter long, so you can almost always find something good to see.

254 W 54th St; various prices plus $25 food/drink minimum

Caroline’s may be bigger and UCB more hip, but it’s hard to beat this Greenwich Village institution when it comes to star power. Unlike most comedy clubs, the Comedy Cellar operates on a showcase format, which—along with its small size—makes for a much more casual, intimate experience than most places where Louis C.K. and Dave Chappelle perform. Oh, yeah, they pop in regularly (and randomly)—along with guys like Marc Maron, Colin Quinn and Artie Lange. Even Jerry Seinfeld, Chris Rock and Jon Stewart have been known to casually sneak on stage for a few minutes of stand-up. Go on a Monday or Tuesday if you can—the big names often pop in early in the week, when crowds are less touristy.

117 Macdougal Street; $12–$24 plus two-drink minimum