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15 Delicious Bourbon Cocktails You'll Want to Sip All Winter

These bourbon drinks will have you feeling cozy all season long.

If you're drinking and getting cozy by the fire, grabbing a beverage for a holiday movie night, or meeting old friends at the bar on a snowy day, no alcohol says winter quite like bourbon. Just one sip of bourbon whiskey will warm you right up on even the coldest days. Some people drink it neat, some enjoy it on the rocks, while others prefer a flavorful bourbon cocktail.

For those who prefer a cocktail, the options are endless. Drinks like an old fashioned, Manhattan, Mint Julep, Whiskey Sour, Paper Plane, and Hot Toddy all use bourbon as the base to bring out the unique qualities of each cocktail that people love so much.

While these classics are solid go-tos for any occasion, some whiskey drinkers may want to take it up a notch during the winter months with a more festive, seasonal approach. Read on to discover some delicious winter-themed bourbon cocktails that can keep you feeling toasty for the next few months. And for more on drinks, check out 10 Cocktails Bartenders Actually Order.

Spicy Bourbon Pumpkin Smash

Pumpkin bourbon smash
Half-Baked Harvest

Homemade pumpkin spice syrup, orange juice, bitters, ginger beer, and your bourbon of choice all come together to make this Spicy Pumpkin Smash. People most often associate pumpkin with fall, but these flavors can keep you warm and cozy all winter long, too.

Get the recipe from Half-Baked Harvest.

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Vanilla Chai Old Fashioned

Vanilla Chai Old Fashioned
Half-Baked Harvest

You can't go wrong with a cocktail made up of toasty vanilla, spicy chai, and warming bourbon. Keep your guests feeling cozy or make this one for you and your loved ones to make the long winter nights a bit brighter. All you need to do ahead of time is make a chai simple syrup from chai tea bags, sugar, and water, which you can keep in the fridge for future drinks!

Get the recipe from Half-Baked Harvest.

Brown Sugar Bourbon Smash

Brown sugar bourbon smash
How Sweet Eats

This Brown Sugar Bourbon Smash feels like the cocktail version of your favorite holiday desserts, with flavors like ginger, brown sugar, apple, and cinnamon. It may be served over ice, but this winter bourbon cocktail will warm you right up.

Get the recipe from How Sweet Eats.

A Long Winter's Nap

A Long Winter's Nap
Feasting at Home

This bourbon cocktail, appropriately called A Long Winter's Nap, can be served either chilled or hot and features a satisfying combination of flavors of maple, ginger, anise, lemon, cinnamon, and bourbon.

Get the recipe from Feasting at Home.

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Winter Bourbon Smash

Winter Bourbon Smash
Minimalist Baker

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

Get the recipe from Minimalist Baker.


Gimme Some Oven

You can sip on a Boulevardier year-round, but this simple bourbon-based recipe featuring orange, Campari, and sweet vermouth can warm your insides right up during the coldest months.

Get the recipe from Gimme Some Oven.

Holiday Cheermeister Bourbon Punch

bourbon punch
Courtesy of Half Baked Harvest

This holiday-inspired punch features some of your favorite winter flavors of pomegranate and orange, combined with bourbon and Prosecco. This bourbon cocktail is great for impressing a party, and you can even add a sprig of rosemary for a fancy touch.

Get the recipe from Half-Baked Harvest.

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Chili Cinnamon Bourbon Hot Toddy

cinnamon hot toddy
Courtesy of Minimalist Baker

A hot toddy is a classic winter beverage for when you need to warm up, and it's also a popular cold remedy for those who want a little kick of bourbon to help them feel better. This recipe resembles the traditional hot toddy but features cinnamon and red chili pepper for extra spice.

Get the recipe from Minimalist Baker.

Spiced Honey Bourbon Old Fashioned

spiced honey old fashioned
Courtesy of Half Baked Harvest

This recipe is similar to a classic old fashioned, but with a seasonal twist. You'll enjoy cozy flavors of cinnamon, cardamom, rosemary, and honey, along with your favorite bourbon of choice.

Get the recipe from Half-Baked Harvest.

Bourbon Lemon Rosemary Sour

Bourbon lemon
Foxes Love Lemons

This bourbon cocktail is one of the lighter, more refreshing options on the list, for those who don't want something super heavy and boozy. It's like your typical sour, but with some rosemary-infused simple syrup to balance out the tart citrus flavors. This one is sure to impress those who love lemon and bourbon together.

Get the recipe from Foxes Love Lemons.

Cranberry Bourbon Sour

Cranberry bourbon sour
Courtesy of Half Baked Harvest

Another take on a whisky sour, but this time with the seasonal flavor of cranberry and orange. This one also goes great with a sprig of candied rosemary on top, which is a move that will make you look like a professional bartender with very little effort at all.

Get the recipe from Half-Baked Harvest.

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Hot Buttered Bourbon

buttered bourbon
Courtesy of Well Plated By Erin

Hot buttered bourbon is a delicious cozy drink that will warm you right up from the inside out. It combines apple cider, butter, a variety of spices, honey, and bourbon, and this drink can be stored in the refrigerator and reheated again whenever you'd like.

Get the recipe from Well Plated By Erin.

Cinnamon Bourbon Old Fashioned with Brûléed Oranges

cinnamon bourbon old fashioned
Courtest of Half Baked Harvest

This is another rendition of an old fashioned, but this time with homemade cinnamon simple syrup, orange juice, and brûléed oranges. Making brûléed oranges is simple and requires very little effort, but is a detail that makes this drink unique.

Get the recipe from Half-Baked Harvest.

Cinnamon Maple Whisky Sour

maple whiskey old fashioned
Courtesy of Cookie + Kate

This recipe is simple and requires only four ingredients, so it's a great choice for beginner at-home bartenders. Just grab your bourbon of choice, maple syrup, lemon, and ground cinnamon, and you've got yourself a cozy winter cocktail.

Get the recipe from Cookie + Kate.

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Autumn Apple Bourbon Fizz

autumn apple bourbon fizz
Courtesy of How Sweet Eats

Yes, this is technically an autumn-themed cocktail, but the recipe is too cozy and delicious to not include on your list of winter drinks. The use of flavors like apple, cinnamon, orange, fig, and ginger makes for a great cold-weather bourbon cocktail to try on your own or share with friends.

Get the recipe from How Sweet Eats.

This article has been updated since its original publish date to include additional entries, proofreading revisions, and additional contextual links.

Samantha Boesch
Samantha was born and raised in Orlando, Florida and now works as a writer in Brooklyn, NY. Read more about Samantha