The Best 6 Bourbon Cocktails to Sip Throughout the Winter

Nothing says winter quite like bourbon, whether you're meeting old friends at the bar on a snowy day, enjoying a drink while cuddling up by the fire, or both.

On the coldest days, just one sip of bourbon whiskey will instantly warm you up. Some like it neat, some on the rocks, and still others would rather have a good bourbon cocktail.

Spicy Bourbon Pumpkin Smash

This Spicy Pumpkin Smash combines homemade pumpkin spice syrup, orange juice, ginger beer, bitters, and your preferred bourbon. 

Vanilla Chai Old Fashioned

A cocktail consisting of warming bourbon, spicy chai, and toasty vanilla can't go wrong. Make this for you and your loved ones to enjoy on the long winter nights, or keep your guests feeling toasty. 

Brown Sugar Bourbon Smash

With flavors reminiscent of your favorite holiday desserts—apple, cinnamon, brown sugar, and ginger—this Brown Sugar Bourbon Smash feels like a cocktail. 

A Long Winter's Nap

A Long Winter's Nap is a fitting name for this bourbon cocktail, which tastes good warm or cold and combines flavors of maple, ginger, anise, lemon, cinnamon, and bourbon.

Winter Bourbon Smash

A traditional bourbon smash would be made with freshly muddled fruit, but to save time and still deliver a burst of comforting flavors for the chilly months ahead, this Winter Bourbon Smash uses fruit preserves along with orange juice and triple sec.


Although you can enjoy a Boulevardier all year round, in the winter months this easy-to-make bourbon-based concoction with orange, Campari, and sweet vermouth will really warm you up.

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