There are a few things that the Flatiron District is known for. One is a building that basically looks like a 22-story doorstop, and another is Madison Square Park (aka the only playground for every child being raised around 23rd Street). If you find yourself in this tiny neighborhood in need of some alcohol, there are a lot of upscale cocktail lounges, but you can also grab beers at a place that encourages you to trash it online (which only makes people love it more). Read about that spot and more in this guide to our favorite places to drink around Flatiron.


This huge Flatiron spot is really three bars under the same roof, and the focus here is on gin. They have more than 180 different kinds on hand, but if you want a Guinness, you can order that too (unless you’re sitting in the wrong place). The somewhat Victorian-themed front area serves drinks that the more upscale “Emerald Bar” in the back doesn’t—and vice versa. There’s also a lounge downstairs with DJs. If you get hungry, try the lemongrass fluke crudo.

Every house cocktail at this speakeasy (under Patisserie Chanson) has some sort of gimmick or theme. For example, the Coconino Rain made with spiced rum and prickly pear is suspended from the ceiling like a house plant, and we genuinely can’t decide if that’s cool or the most ridiculous thing ever. The decor and limited food options (salmon crudo and beef sliders, e.g.) aren’t as interesting as the drinks. There are a few small tables with plush round seats and a long bar with some high chairs for two. We’ve dubbed those “loveseat bar stools.”

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If your idea of a good time is listening to live jazz while drinking hard-to-find whiskey, plan your next night out at The Flatiron Room. This supper club-like place never charges a cover, and if there’s a brown liquor you’ve been searching for, you’ll probably find it in their 55-page binder. Buy a whole bottle, and they’ll tag it with your name, store it, and bring it out for you whenever you come back. You’ll see bottles locked up in cages along the walls in the very dark room, which features a stage with a curtained backdrop lit in different colors along with a bunch of round tables covered in white tablecloths and little lamps.

The original Apotheke in Chinatown is part of the reason why there are speakeasies in every New York City zip code. Now, there’s an Apotheke near Flatiron where you enter through an unmarked door on 26th. The subterranean interior is lit mostly by candlelight, and there are several huge booths along with a central seating area that consists of what is essentially a large, partitioned ottoman surrounded by wobbly stools. Unstable stools aside, this is a fun place to drink, especially if you’re looking for something low-key but fancy.

photo credit: Emily Schindler

This steakhouse has been a London institution for long enough (with enough locations) to have lost some of its intrigue on the other side of the Atlantic, but we say keep the sticky toffee pudding coming. The bar area at Hawksmoor is one of the sexier spaces in the city—it’s all high ceilings, dark wood, and blue leather. Try one of their four “ultimate martinis” or a highball made with bourbon and peach, order a bone marrow cheeseburger, and get that sticky toffee pudding for dessert.

The theme of this bar is quite literally “one star on Yelp,” and that self-awareness works perfectly. Their idea of a bar snack is a Pop Tart, the drinks are kind of cheap but not that cheap, and most people come here to down a serviceable but watery whiskey ginger. The space is about what you’d expect for a place that prides itself on mostly serving beers in cans because bottles are too fancy. There’s a brick wall, some tables and booths, and not much else. Bring your coworkers here, listen to their initial complaints, and feel a sense of pride when you eventually hear that they all want to come back soon.

Undercote is a cocktail bar located beneath Cote, and it feels kind of like the reptile house of an upscale zoo. The space consists of a few small interconnected rooms, the furniture is all black, and there are several walls covered entirely in plants. Cocktails start around $20, and they’re made with everything from chinola and eucalyptus to Thai chili and butterfly pea. There’s also one made with catnip—and it’s surprisingly good. Is it worth $21? It depends on how badly you want to try catnip.

photo credit: Adrian Gaut

Broken Shaker is a rooftop bar, but it feels more like a house party in a nice, beach-themed apartment. It’s on top of the Freehand Hotel, and there’s a big indoor space with plenty of tables and bars, as well as a large wraparound terrace. You can either sit and order food (like some shrimp dumplings and a Cubano), or you can just grab a drink at one of the bars and enjoy the views. That said, it gets crowded here, so you should get here early, or mentally prepare for a long wait. The good news is, it’s worth it.

The Chapel Bar is hidden behind an unmarked door in the lobby of a photography museum called Fotografiska. It’s in a space that was formerly a cathedral, and it has high ceilings and a massive chandelier that probably cost more than the last car you saw on the street. So if you’re looking for an impressive spot to have a quiet conversation with someone over an elaborate cocktail or two, this is a great choice. It’s a small, dark room filled with armchairs, and it feels kind of like a members-only club for Bond villains.


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