12 Warming Whiskey Cocktails to Slow-Sip This Winter

Before I’d ever tried a cocktail, I knew my future with whiskey was bright. It was the prom after-party, and everyone was smashed.I, still in my rumpled prom suit, was taking swigs from a full bottle of Laphroaig Scotch I had borrowed from my parents’ liquor cabinet—I figured they wouldn’t miss it. I remember—just barely—my friend Justin’s dad (hosting on some “chill parenting” or harm-reduction tip) approaching me at the party and telling me, “son, you have good taste in whiskey. All these other kids are gonna have terrible hangovers in the morning, but you’ll be just fine.” With those reassuring words still lingering in my mind, I lay down in the middle of the dining room floor, and passed out.

Ever since this Laphroig-fueled experience, I’ve been a lover of whiskey. Scotch, yes, but also bourbon, rye, Japanese, Canadian, and Irish. Though I will still happily sip a fine whiskey straight or on the rocks (occasionally I’ll even take a swig from the bottle), I now consume most of my whiskey in cocktail-form. As the first snow settles on the eaves, there’s really nothing better than a rich, bone-warming whiskey cocktail or two as you watch the world go by.

Here are 12 timeless, yet traditional, whiskey cocktails.

1. Old Fashioned

The original “Cock-Tail” first written about in 1806, this is not your granny’s old fashioned, with seven sugary cherries and a rock candy stirrer. Fortunately, the craft cocktail movement of recent years has returned the recipe to its boozy, spicy original form. Just whiskey, sugar, bitters, and an orange peel for garnish, this is a drink that keeps the focus on an excellent bourbon or rye.

2. Manhattan

Likely an offshoot of the Old Fashioned, the Manhattan is fortified with sweet vermouth, making for a slightly deeper, earthier profile than its predecessor. Also, with a Manhattan, no cocktail snob will judge you if you plunk in a brandied cherry (or even two).

3. Boulevardier

Perhaps my favorite whiskey cocktail of all, the Boulevardier is another strong, stirred drink featuring American whiskey (bourbon or rye) and sweet vermouth. But it moves further into European territory with the addition of Campari, the bright red bitter of grapefruit and herbs, and, of course, the name. According to Harry Elhone, the former owner of Harry’s New York Bar in Paris, it was developed by Erskine Gwynne, the American publisher of a Parisian expat newspaper that shared its name. Though most often built on bourbon, I think it’s best with a spicy rye.

4. Old Pal

Another cocktail served in Harry’s New York Bar in Paris in the 1930s, the Old Pal was developed by Harry himself, as a drier, more aggressive riff on the Boulevardier. With rye in place of the typical bourbon, and dry instead of sweet vermouth, this is not a drink to be ignored. Even more than usual, my advice here is to reach for the top shelf: The harsh alcohol notes of a cheap whiskey or the briny tang of a bad vermouth will really hit you over the head with this one.

For another dry vermouth and rye cocktail, try a Session Manhattan

5. Vieux Carré

Like its eponymous New Orleans neighborhood, this robust stirred drink is an appealing collision of loud, boozy flavors. There’s rye, bitters, and vermouth, as well as Bénédictine and cognac, dancing under a lemon twist.

6. Sazerac

While we’re in New Orleans, here’s another storied cocktail from The Big Easy with a wild streak. In the Sazerac, a drink that traces its lineage to the Sazerac coffee house in the mid-1800s, rye is set off with a dash of New Orleans’s own Peychaud’s bitters and a bar spoon of absinthe.

7. Mint Julep

Whiskey drinks are not, you may be relieved to hear, all boozy and complex. The spirit also has a lighter side, perhaps best represented by the foppish Julep, served sweet and cold over crushed ice in a tin cup brimming with mint. Though in the 1700s mint juleps were prescribed for nausea, this probably did not have the desired effect—these quaffable concoctions pack a punch.

8. Whiskey Sour

Technically a Boston sour if you add the egg, the classic combination of bourbon, simple syrup, and lemon with a foamy egg white head is classy, but in a casual, summery way. Drink a Whiskey Sour on your fire escape, but maybe tether yourself in before you have a second round.

9. Paper Plane

A new classic of the craft cocktail revival, Sam Ross’s Paper Plane is an equal parts drink that splits the difference between the somber whiskey-soaked mixology of the early 2000s and the recent Aperol craze, making for a bright and balanced drink.

10. Irish Coffee

Another whiskey cocktail that makes for easy drinking (often too easy), the Irish Coffee doesn’t take itself too seriously. But it’s a seriously delicious cocktail all the same. Made, naturally, with Irish whiskey—much milder than its American cousins, after triple-distillation and aging in used oak barrels. Irish coffee is really all about the contrast of hot, boozy coffee and cold, fresh cream. Though it’s not as ubiquitous in Ireland as in the U.S., my wife, a Corkonian, assures me it’s known as Irish Coffee even in the motherland.

11. Rob Roy

A quick paddle across the Irish Sea, and you’re in the land of Scotch. Though there are a wide range of styles, my favorites are saturated with peat smoke and smell like my grandpa (or is it the other way around?). The Rob Roy picks up where the Manhattan left off, swapping Scotch for bourbon to make the sort of smoky, boggy winter drink that belongs near roasting chestnuts and an open fire.

12. Penicillin

Another modern classic from Sam Ross, this is a cure-all with a serious kick. Lemon and ginger are good for you, sure, but the key is a quarter-ounce of peat-smoked Laphroig. Don’t worry if you knock back a few of these in a night, you’ll be fine in the morning—just ask Justin’s dad.

For a similar spicy-sweet drink, try a Bourbon, Orange, and Ginger .

Which whiskey cocktails do you like to make? Tell us about them in the comments!