31 Whiskey Cocktails to Sip No Matter the Season
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There are some whiskey cocktails that lend themselves to cooler weather: manhattans, old-fashioneds, boulevardiers…. Others, like a whiskey sour or a mint julep, lean into summer (though, frankly, a whiskey sour makes for an excellent Thanksgiving cocktail as well). Whatever time of year it is where you are, there is a whiskey drink just right for the occasion.
Below you'll find a handful of our favorites made with rye, bourbon, scotch, and Irish whiskey. If you find one you absolutely love, feel free to play around with it. Try the same classic cocktail with a few different bottles of whiskey, or branch out into one of its many riffs. Make a big batch to share with friends or stir up a drink to enjoy on your own with a vintage cocktail book at your side.
Photo by Joseph De Leo, Food Styling by Michelle Gatton1/31Old-Fashioned
The old-fashioned is about as classic as whiskey cocktails get, but there are still disagreements about how to make a good one. This version uses simple syrup to avoid grit, though many swear by a bitters-soaked sugar cube instead. Rye or bourbon? That’s your choice. You don’t need a mixing glass for this drink; you’ll make it right in the rocks glass or old-fashioned glass you’ll sip from.
Photo by Joseph De Leo, Food Styling by Michelle Gatton. Glassware by Riedel.2/31Manhattan
The manhattan cocktail dresses up whiskey with luscious sweet vermouth, plus a few dashes of Angostura bitters and/or orange bitters. It’s a great, simple vehicle for trying out new bottles—your best whiskey will shine in this drink. Look for high-quality maraschino cherries for the garnish.
Photo by Kelly Puleio3/31Newton's Law
This easy whiskey recipe 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.
Photo by Travis Rainey, Food Styling by Tiffany Schleigh6/31Boulevardier
Many of the greatest drinks are truly simple. And some of those reward a lifetime of experimentation. Try this classic boulevardier recipe, then try splitting the portion of Campari among your favorite bitter liqueurs.
Photo by Joseph De Leo, Food Styling by Micah Marie Morton7/31Penicillin
It’s not shocking that this newish invention has become a modern classic; it’s hard to find someone who doesn’t like the combination of whiskey and ginger. For a fizzy spin, try the Fleming Fizz, which adds sparkling wine to the formula.
Photo by Andy Sewell8/31Fanciulli
If you read our After Hours newsletter, you know that this crisp take on the manhattan is a new favorite of ours. There’s just a touch of pungent fernet in the mix, but it adds worlds of botanical flavor.
Photo by Kelly Puleio10/31Sneaky 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.
Photo by Joseph De Leo, Food Styling by Rebecca Jurkevich11/31Paper Plane
This simple, citrusy, slightly bitter concoction is one of our all-time favorites—if you haven’t tried this new-classic whiskey drink, 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.
Photo by Joseph De Leo, Food Styling by Judy Haubert, Prop Styling by Anne Eastman12/31Bow & Arrow
This tangy hidden gem of a cocktail mixes bourbon with mezcal, plus pineapple, cinnamon, and fresh lime juice.
Photo by Elizabeth Coetzee, Food Styling by Judy Haubert13/31Blinker
Need more 3-ingredient cocktails in your repertoire? This combo of rye whiskey, fresh grapefruit juice, and grenadine is a guaranteed crowd-pleaser.
Photo by Travis Rainey, Food Styling by Emilie Fosnocht14/31Irish Coffee
This classic drink requires hot, strong coffee, Irish whiskey, and freshly whipped cream. It’s the perfect winter sipper for serving with warm homemade cookies.
Photo by Joseph De Leo, Food Styling by Micah Marie Morton16/31Fireplace Eggnog
This modern twist on classic eggnog is, quite honestly, one of the best holiday drinks we’ve ever tried. It’s made with the traditional mix of dairy and eggs, plus smoky tea, high-proof bourbon, aged rum, and a touch of port. Prep a batch in advance and keep it in your fridge.
Photo by Joseph De Leo, Food Styling by Sean Dooley17/31The Godfather Sour
Rev up your amaretto sour with a touch of smoky scotch. We like it with a large ice cube and curled orange-peel rosette—optional, but fun if you’re trying to dial in your cocktail garnish game. You’ll use one egg white for every two drinks here so the flavors really shine.
Photo by Paul H. Christian, Food Styling by Michele Figliuolo18/31Mint Julep
This version of the classic julep gets invigorating flavor from a fresh mint syrup that’s strained for easy drinking. If you don’t have a fridge or countertop ice machine to make pebbled or crushed ice, have a friend help out with some smashing prior to your next Kentucky Derby party.
Photo by Joseph De Leo, Food Styling by Kaitlin Wayne20/31Cowboy Killer
This smoky variation on the Brooklyn cocktail is made with anise-scented Peychaud’s bitters, almondy maraschino liqueur, and peaty Islay scotch. It’s the kind of thing you want to drink in front of a roaring fire, with a salty snack close at hand. You’ll express the lemon peel over the top to add its oils to the drink, but then discard before sipping.
Photo by Joseph De Leo, Food Styling by Kaitlin Wayne21/31Bizzy Izzy Highball
This whiskey and sherry drink, made with fresh pineapple and lemon, feels completely modern, but it's actually over 100 years old.
Photo by Paul H. Christian, Food Styling by Michele Figliuolo29/31Vieux 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.
