Whiskey

63 Whiskey Cocktails to Get You Through Winter

There are many, many ways to enjoy whiskey season.

November 7, 2021

63 Whiskey Cocktails to Get You Through Winter

In chilly weather we find ourselves gravitating to whiskey cocktails: Manhattans, old-fashioneds, Boulevardiers, and other classic drinks. But if you believe that whiskey has a season, then that season is the perfect time to play around with drinks and riffs you haven’t tried before. Whiskey pairs wonderfully with spice and cold-weather fruit, with bitter liqueurs and rich and creamy drinks. Hot toddy recipes? We’ve got more than a few options for those as well. Below you’ll find 63 of our very favorite whiskey drinks, including cocktails made with rye, bourbon, scotch, and Irish whiskey. Make a batch to share with friends or stir up a drink to enjoy on your own with a good book at your side.

Photo by Joseph De Leo, Food Styling by Anna Stockwell
1/63
Scotchy Boulevardiers
Meet the Negroni’s wintery cousin—a combination of rye whiskey and Scotch in place of gin makes this whiskey cocktail peppery and rich, with a touch of smoke. Our recipe makes 8 servings, which you can keep in the freezer for about 2 weeks. Think of it as meal planning for your home bar—a great way to get your Thanksgiving cocktails ready in advance.
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Photo by Joseph De Leo, Food Styling by Michelle Gatton
2/63
Old-Fashioned
The Old Fashioned is about as classic as whiskey drinks get, but there are still disagreements about how to make a good one. This one uses simple syrup to avoid grit, though many swear by a bitters-soaked sugar cube, instead. Rye or bourbon? That's your choice.
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Photo by Joseph De Leo, Food Styling by Michelle Gatton. Glassware by Riedel.
3/63
Manhattan
The Manhattan cocktail is a classic whiskey sipper made with sweet vermouth and orange or Angostura bitters. It's a great, simple vehicle for trying out new whiskeys (or vermouths). Look for high-quality maraschino cherries for the garnish.
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Photo by Kelly Puleio
4/63
Newton's Law
This easy whiskey recipe from our digital director Maggie Hoffman's first book, The One-Bottle Cocktail, begins with bourbon and fresh lemon juice, sweetened with a touch of brown sugar and spiced apple butter, which you can buy or make from fresh apples.
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Photo by Joseph De Leo, Food Styling by Micah Marie Morton
5/63
Penicillin
It's not shocking that this new-ish invention has become a modern classic; it's hard to find someone who doesn't like the combination of whiskey and ginger.
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Photo by Joseph De Leo, Food Styling by Lillian Chou
6/63
Paradise Apple
This one tastes like fall in a glass: Dry riesling adds tangy, fruit flavor to a mix of bourbon, dried figs, honey, elderflower liqueur, and fresh apple cider. Serve in a stemmed glass and garnish with a dehydrated apple to really complete the look.
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Photo by Chelsea Kyle, Prop Styling by Alex Brannian, Food Styling by Ali Nardi
7/63
Mike's Milk Punch
Try this frothy, creamy cocktail instead of eggnog to kick off your Christmas festivities.
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Photo by Joseph De Leo, Food Styling by Michelle Gatton
8/63
Sazerac
This is a stiff drink that's especially popular in New Orleans. Herbsaint came into common use when absinthe was outlawed, but feel free to use absinthe in your Sazerac instead if you have it on hand.
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Photo by Paul H. Christian, Food Styling by Michele Figliuolo
9/63
Mint Julep
A classic whiskey cocktail made with bourbon and mint is even more fragrant when you flavor your simple syrup.
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Photo by Joseph De Leo, Food Styling by Judy Haubert
10/63
Classic Whiskey Sour
If you've never had this classic drink made without sour mix, you're in for a treat.
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Photo by Joseph De Leo, Food Styling by Michelle Gatton
11/63
That’ll Take the Edge Off
This Sazerac-inspired cocktail is boozy, herbal, and Scotchy. Some of our editors—shhhhh!—might even prefer this riff over the classic version.
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Dan Monick
12/63
The New York Sour
A red wine float turns the classic, summery whiskey sour into a cold-weather favorite.
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Photo by Kelly Puleio
13/63
Sneaky Peat
Cranberry punch recipes are often simple, fruity, and one-dimensional. But this one's a full-on cocktail in a big bowl, pairing the tangy cranberries with oolong tea that’s been steeped a long, long time so it has a ton of tannin and a touch of bitterness. The central spirit: Scotch whisky, which gives the drink a bit of smoky, malty complexity.
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Photo by Peden & Munk
14/63
Manhattans By the Pitcher
Why stir individual servings when you can have a pitcher or bottle of cocktails ready to pour?
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Photo by Antonis Achilleos
15/63
Going Out West
Looking for an after-dinner option? This recipe features spicy rye, smoky mezcal, and luscious Averna Amaro. Add an orange twist for the aroma.
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Photo by Joseph De Leo, Food Styling by Michelle Gatton. Glassware by Riedel.
16/63
Little Italy
Lovers of the Manhattan should try this variation from Audrey Saunders of Pegu Club in NYC. It starts with rye and vermouth, then adds Cynar—a bittersweet Italian liqueur you might recognize by the artichoke on the label—for deep, vegetal bitterness.
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Photo by Paul H. Christian, Food Styling by Michele Figliuolo
17/63
Vieux Carré
Named for the French Quarter of New Orleans, this classic cocktail is multilayered and boozy. It's made with rye, cognac, sweet vermouth, and Bénédictine, an herbal liqueur that's sweetened with a touch of honey.
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Photo by Joseph De Leo, Food Styling by Drew Aichele
18/63
Blood and Sand
The important thing to remember about this equal parts cocktail is that it's not a sour. That said, extra-tart and bitter Seville oranges make an amazing version, if you're able to find them.
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19/63
The Celtic Buck
Pear, allspice, ginger, and cinnamon come together in this fizzy Scotch cocktail from Julie Reiner of New York's Clover Club.
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Photo by Joseph De Leo, Food Styling by Micah Marie Morton
20/63
Fleming Fizz
This fizzy cocktail, made with Scotch, lemon, and sparkling wine, isn't at all shy. It's packed with fresh ginger for a spicy kick.
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Photo by Paul H. Christian, Food Styling by Michele Figliuolo
21/63
Hot Toddy
Do you like a toddy best with Scotch? With bourbon? With rye? Winter's a great time to test all the options.
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Photo by Paul H. Christian, Food Styling by Michele Figliuolo
22/63
Brown Derby
A simple drink, and simply delicious. Bourbon meets fresh grapefruit juice and honey syrup in perfect balance.
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Photo by Joseph De Leo, Food Styling by Micah Marie Morton
23/63
Turmeric Hot Toddy
This soothing hot toddy from bartender Claire Sprouse of Brooklyn’s Hunky Dory is wonderfully savory from the combination of nutty Amontillado sherry and earthy turmeric. You can make it with almost any spirit, but we especially like it with bourbon. Bring it out to the backyard and sit around the fire pit.
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Photo by Kelly Puleio
24/63
Islay and Olive
If you like dirty martinis, this might be the whisky cocktail for you. Made with peaty Scotch and olives three ways, it's super-savory.
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Photo by Andrew Purcell
25/63
Slow-Cooker Star Anise–Black Pepper Hot Toddy
This festive, spiced toddy starts with a black tea base. English breakfast tea is especially good with the black pepper and star anise, but Earl Grey would be nice, too.
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26/63
Irish Coffee
This classic drink requires hot, strong coffee, Irish whiskey, and freshly whipped cream. It's the perfect winter drink for serving with your favorite homemade cookies.
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Photo by Joseph De Leo, Food Styling by Rebecca Jurkevich
27/63
Paper Plane
This simple, citrusy, slightly bitter concoction is one of our all-time favorites—if you haven't tried one, be sure to put it on your list. It's made with equal parts citrusy Amaro Nonino, Aperol, bourbon, and fresh lemon juice, shaken together with ice and strained into a coupe glass.
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Photo by Paul H. Christian, Food Styling by Michele Figliuolo
28/63
Gold Rush
Here's a super-simple whiskey recipe: Bourbon, fresh lemon, and honey, shaken well. It's a whiskey drink that'll please lovers of fresh, tart cocktails, too.
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Photo by Chelsea Kyle, Prop Styling by Astrid Chastka, Food Styling by Anna Stockwell
29/63
Raspberry and Thyme Hot Toddy Punch
The hot toddy goes large-format here. Fresh thyme and raspberry liqueur make it special.
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30/63
Sforzando (Whiskey and Mezcal Cocktail)
Some whiskey cocktails benefit from a second layer of spirits. In this Manhattan variation, rye and mezcal team up for complex, earthy flavor.
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Photo by Bobbi Lin
31/63
Earl Grey–Bourbon Punch
To make a decorative ice ring, freeze citrus slices and fresh herbs with water in a cake pan or Tupperware that fits inside your serving vessel. Pomegranate seeds look nice, too!
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Photo by Roland Bello
32/63
Perfect Manhattan
It's easy to love this version of the classic drink, but that's not why it's called “perfect”—that word refers to the mix of sweet and dry vermouth called for in the recipe.
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Photo by Danny Kim
33/63
Sage Brown Derby
A little sage brings out the peppery, herbal flavors of the classic combination of whiskey and grapefruit juice.
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Photo by Marcus Nilsson
34/63
Bourbon Fruit Tea Punch
Bourbon-spiked black tea with fresh orange, pineapple, and tart lemon juice. This recipe makes eight servings, though you can easily cut it in half for a smaller crowd.
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Photo by Ted Cavanaugh
35/63
The Rattlesnake
You'll get a bit of a workout shaking this drink. The first shake—without any ice—breaks up the egg white, while the second chills and properly dilutes the cocktail.
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Photo by Andrew Purcell, food styling by Carrie Purcell
36/63
The Smoky Robinson
A boozy whiskey cocktail that's equal parts mezcal smoke and festive sweetness, thanks to a warm, spice-infused maple syrup.
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Levi Brown
37/63
Rye Witch
Rye whiskey, orange bitters, and nutty Amontillado sherry mingle in this incomparably smooth cocktail. Chilling the coupe glasses in your freezer will help the drink stay cool longer.
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Photo by Kelly Puleio
38/63
Spanish Penny
This pantry cocktail pairs whiskey (100-proof rye is preferred) with maple syrup and a touch of sherry vinegar for brightness. Serve in a rocks glass.
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Photo by Romulo Yanes
39/63
Tipperary
Named for a county in Ireland, this cocktail is made with Irish whisky and emerald-green herbal Chartreuse liqueur.
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40/63
Old Pal
If you like bittersweet Campari, give this one a try, especially if you have some high-proof bourbon around.
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Photo by Paul H. Christian, Food Styling by Michele Figliuolo
41/63
Cold Toddy
Almost anything can be toddied. But did you know a hot toddy can also be… cooled? For a more refreshing tipple, take down the temp. Earl Grey tea adds citrusy fragrance, while fresh ginger adds spice.
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42/63
Whiskey Flip
Grate a little nutmeg on top of this creamy, rich concoction. You could also add a touch of good rum to the mix.
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William Hereford
43/63
Conference
Tiki drinks often layer multiple spirits for complex flavor. Here, the technique is applied to a stirred, boozy drink with fantastic results.
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Photo by Chelsea Kyle, Prop Styling by Beatrice Chastka, Food Styling by Kate Schmidt
44/63
Cherry-Bourbon Soda Can Cocktail
Adding bourbon and Campari to cherry cola makes for a sweet, spicy, and refreshing drink, no cocktail shaker required.
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Photo by Paul H. Christian, Food Styling by Michele Figliuolo
45/63
Strawberry, Grapefruit, and Chamomile Brunch Punch
The tart punch of grapefruit balances this combination of bourbon, chamomile, and bitters. It's an easy-drinker, so go slow.
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46/63
Uncle Angelo’s Eggnog With Bourbon and Rum
Think you're not into eggnog? This light-as-clouds version may convince you.
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Photo by Ed Anderson
47/63
Thunderer
A little heat, a little tangy brightness, and the warmth of your favorite bourbon—this spicy drink is a crowd-pleaser.
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Photo by Chelsea Kyle, Food Styling by Matt Duckor
48/63
The Maple-Ginger Hot Toddy
Brewed tea is an easy way to infuse complex flavors into warming winter cocktails like this one.
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Photo by Chelsea Kyle, Food Styling by Anna Stockwell
49/63
Maple Old-Fashioned
A touch of earthy maple syrup makes the classic Old Fashioned perfect for a cold-weather bonfire. (It also means you don't need to dissolve any grainy sugar in the mix.)
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Photo by Julie Soefer
50/63
Old Pepper
A little Crystal hot sauce and three dashes of Worcestershire sauce give this bourbon cocktail savory staying power.
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Teri Lyn Fisher
51/63
Bobby Burns
Scotch, sweet vermouth, and Benedictine make a luscious, herbal cocktail. This version makes eight drinks, but it'll keep a few weeks in the fridge.
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Gentl & Hyers
52/63
Trouble in Paradise
This citrusy Campari and bourbon drink gets a little black pepper and fresh basil in the cocktail shaker.
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53/63
Boulevardier
This recipe amps up the whiskey a bit, making for a Boulevardier that's a bit less sweet than standard. It's a great way to go.
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Photo by Andy Sewell
54/63
Kentucky Buck
Bookmark this one for spring: strawberries shine in this tall, refreshing, gingery cocktail, made with bourbon, fresh lemon, muddled berries, and spicy ginger beer.
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Ma'ayan Rosenzweig
55/63
Rabbit Punch
This cocktail starts with an oleo-saccharum, which is a fancy name for a syrup that's made with citrus peels and sugar sitting together for a few hours. Pineapple adds tropical fragrance, while sparkling wine gives it all a festive lift.
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Jamie Chung
56/63
Honey-Bourbon Toddy
To make a truly sublime version of this hot toddy, combine sliced apples, a bottle of bourbon, and some cinnamon sticks in a pitcher in your fridge for a few days before you begin.
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Sheri Giblin
57/63
Rittenhouse Inn Wassail Punch
Amp up your apple cider with tart cranberry juice, bourbon, ginger, allspice, and cloves. A quick simmer brings it all together.
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58/63
Rob Roy
Essentially, this is a Manhattan, but with Scotch. If you have a few different bottles around, consider mixing two different versions: something mellow and something peaty.
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Photo by Laura Murray
59/63
Cowboy Shandy
Beer is a great way to make cocktails more fizzy and refreshing. Here, lager and fresh lemon meet High West's Campfire Whiskey (a blend of bourbon, rye, and peated whiskey). If you don't have that bottling, you could make your own blend.
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Photo by Chelsea Kyle
60/63
Goodnight, Irene Cocktail
If you're looking for easy whiskey cocktails that you build right in your flask, you've come to the right place.
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Photo by Ed Anderson
61/63
Up-to-Date Cocktail
Manhattanesque in both composition and deliciousness, this whiskey and sherry welcomes swapping in bourbon if you prefer your drink a little sweeter.
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Photo by Annabel Mehran
62/63
Backwoods Bourbon Punch
Grenadine is the sweetener for this whiskey-grapefruit punch. Buy a good version, or make your own using bottled pomegranate juice—it's not hard!
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Photo by Paul H. Christian, Food Styling by Michele Figliuolo
63/63
Evan's Champagne Julep
This take on the julep feels especially festive; it's one of those whiskey cocktails that's ideal for ringing in the new year. Use a sparkling wine that you enjoy drinking on its own; bad bubbles can't really hide here.
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