The Founder of Women Who Whiskey Takes Us on a Winter Bar Crawl

In a city with over 1,500 bars, she wants to send you to the best.

In a city with over 1,500 bars, even if you narrow down your search by neighborhood, it’s still not always easy to choose a place to enjoy a drink, especially in the snowy dead of winter when barhopping is no longer a practical option.

At Women Who Whiskey, we are always on the lookout for the best new (and old) spots, and hope to help take some of the guesswork out of your search for a better bar. Here are a few of our favorites in Manhattan, with the caveat that this list could go on and on.

For Cocktails

The Gilroy (Upper East Side)

Just a few years old, The Gilroy is the kind of place that seems like it’s been there forever. Without any of the gaudy flourishes that too often mark bars trying to stake their place in the Prohibition-era cocktail bar revival trend, it’s an unassuming but elegant spot in the Upper East Side that starts the evening off quietly but slowly grows to an exciting hum as the night drinks on. It boasts a modest but impressive spirits collection, and an even better cocktail menu.

Known for its Negronis, the Gilroy does not disappoint, featuring almost a dozen creative Negroni variations, including three whiskey versions: the Old Oscar (Larceny Bourbon, Averna, Ancho Reyes, Campari, Aztec Chocolate Bitters), the Old Pal (Old Overholt Rye, Lillet Blanc, Dubonnet Rouge, Campari), and the Boulevardier (Larceny Bourbon, Cynar, Aperol, Bitters). But whiskey lovers should venture out and try the rest of the menu, or just ask the friendly and talented bartenders for a recommendation; they’re talented enough to mix up a classic, or even riff on one. Cocktails $14; serves food.

Manhattan Cricket Club (Upper West Side)

Upstairs from Burke & Wills, The Manhattan Cricket Club has an old-world, speakeasy-esque vibe, reminiscent of Colonial-era gentlemen’s clubs. A membership club open to the public, inspired by Australian cricket clubs from the turn of the century, reservations are only available to members; non-members may access on a walk-in basis. They have a list of House Rules that they’d like you to adhere to, including a dress code. But the Manhattan Cricket Club just manages not to take itself too seriously, with that subtle nod to the tongue-in-cheek that Australians are so good at.

The space itself is small but well designed, with the restored apartment it occupies giving you the feeling of having a drink in someone’s fancy living room. In fact, it’s the perfect spot for a cozy cocktail on a cold winter’s eve. Their house cocktails are eclectic and heavy on the vodka Salt And Pepper (Boyd & Blair Potato Vodka, Garden Tomato Essence, Smoked Black Pepper & White Truffle Mist), but they are also masters of the classics. I enjoyed one of the best Boulevardiers I’ve ever had here. The A Drink In The Hand Is Worth Two In The Bush (Honey bush-Infused Virgil Kane High Rye Bourbon. Cappelletti Aperitivo, Dolin Rouge, Orange Bitters) is barrel aged, resulting in a harmonious mellowing of flavors. Cocktails $12–16; serves Food.

For Drams

On the Rocks (Hell’s Kitchen)
On the Rocks is one of my favorite bars in New York. At first glance, there’s nothing particularly remarkable about it; it’s your standard long and narrow railroad-style space, with barely enough room to squeeze past the bar on your way to the bathroom. But then you start to notice the things that make it special. There are two seats facing the front window, the perfect place to have some privacy in a crowd. There’s a tiny room past the bar, the perfect place to gather a small group of friends that’s still too large to line up at the counter. And most importantly, there’s the shelf of whiskey. Filling practically the entire back wall, there are no duplicates; each one of those hundreds of bottles is something different and magical. Then the bartender hands you a binder where you can flip, flip, flip through lists of whiskeys from all over the world. The staff is knowledgeable and eager to educate, so be prepared to ask some questions about the whiskey list. If you ask nicely, they might even let you try it before you buy it.

They don’t have a cocktail list, per se, but the bartenders are skilled and accommodating, and they’ll make you any cocktail you want with any whiskey you want, adjusting the price based on the cost of the dram. But this place isn’t about the frills, so keep it classic: Manhattans, Old Fashioneds, Sazeracs. You’ll be happy you did.

And if you’re lucky, you’ll end up there on a night when Howie, the owner, is hanging out. A dyed-in-the-wool New Yorker with stories for days, Howie always manages to keep me at the bar longer than I meant to stay. Prices vary; doesn’t serve food.

Copper & Oak (Lower East Side)

Full disclosure: I haven’t been to Copper & Oak. Yet. But since its opening a couple of years ago, it has established itself as the downtown place, par excellence, to explore a stunning variety of spirits without the pretension, so it seemed irresponsible to leave it off this list. For what it’s worth, I’ve heard only good things. The little sister to TriBeCa’s The Brandy Library, it boasts a wide (if not comparable) selection of brown spirits—whiskey, brandy, rum, tequila & mezcal—available in 1oz and 2 oz pours. This allows you to create any combination of flights or tastings, according to your own whims, or the recommendation of the expert bar staff.

Copper & Oak’s approach to drinking is rather purist. Rumor has it they won’t serve you anything in your spirit beyond ice, water, soda, or a simple mixer like ginger. The point is to explore the spirits in their most basic form, getting to know and enjoy them as they are before you gussy them up with bitters and Vermouth. Like On the Rocks, Copper & Oak is the place to hang out for a bit while you figure out what you like, or find new whiskeys to love. Prices vary; serves small plates.

For Cocktails and Drams

Flatiron Room (Flatiron)

Who else is tempted to set these babies free? Photo credit: @davebredesen on IG #theflatironroom #whiskey #nyc

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Flatiron Room doesn’t need any more publicity than it already gets, but it truly is one of the premier cocktail and whiskey bars in New York, with nightly live music (usually jazz) to boot. They also have a bottle locker service, where if you buy a full bottle of your choice of spirit, they will keep it in a locker for you, making it available whenever you and your party want to partake. Boasting one of the most extensive whiskey selections not only in the city but in all the East Coast, Flatiron Room also manages to have one of the best cocktail menus around, with seasonal cocktails, classics and Flatiron favorites.

The 37 West 26th (Black Bottle Scotch mixed with fresh fig, Drambuie, lime, sugar, Peychaud’s Bitters) is divine—perfect for warming you up and settling you into your vintage armchair while you watch a sequined warbler work the stage. Though a simple classic, the Rye Old Fashioned (Rye whiskey, Demerara Sugar, Angostura Aromatic Bitters, orange essence) is elevated out of the ordinary by the orange essence. Flatiron Room is usually buzzing, so it may not be the best place to buttonhole the bartender for a whiskey 101, but it’s a great place for a romantic date or to catch up with a friend. Prices vary; serves food.

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Julia Ritz Toffoli is the Founder & Principal of Women Who Whiskey.