The Best Bourbon Cocktails To Enjoy In The Winter

It's an old saying that drinking a little booze will help warm you up in the winter, but it seems to be even more true in the case of bourbon. A flask of bourbon on a snowy mountain can warm you up just as well as any bonfire or winter coat (it's subjective, but we believe it to be true). Bourbon is the American version of whiskey that is usually mostly comprised of corn which gives the drink a smooth mouthfeel and inherent sweetness (via Bourbon Country). Whether you enjoy a cocktail like an old fashioned or the strong stuff straight on the rocks, it's a staple drink in the wintertime just as much as hot chocolate or eggnog. 

There are endless ways to indulge in bourbon, but some recipes just feel like they warm you up more than others. There are cocktails that honor the in-season fruits of winter or feature some of those warm baking spices that remind many of us of the holiday season. In honor of the change to cold weather, we decided to round up a few of the best bourbon cocktails to enjoy in the winter. There are drinks for even the most novice of bartenders and a few options to challenge yourself that will likely yield a very satisfying reward that warms you from the inside out. 

The Moscow Mule has been a staple on bar menus in America for nearly a century. The origins of the drink that combines vodka, lime juice, and ginger beer in a copper mug are a bit murky, particularly when it comes to who is responsible for the creation (via Wall Street Journal). The consensus is that it originates back to the 1940s at the Cock 'n' Bull pub in New York City. Vodka and ginger beer weren't desired by the American market separately until they were combined, and the rest is history (via Moscow Copper). The vodka version is great any time of the year, but a true winter warm-up is the bourbon version of the cocktail. 

A Kentucky mule is named to honor its bourbon whiskey base, which is the state's signature spirit. The zesty ginger beer brightens up the sweet and smooth bourbon, and the copper mug keeps it ice cold until you're done with it. If you really want to get creative, add some mint leaves or perhaps some apple cider for a fruity touch.  

There are few drinks that will warm you up even on the coldest and snowiest day like a classic hot toddy. It's the boozy alternative to a hot tea that also can help soothe cold symptoms when you're sick. It's believed that the hot toddy originated in British-controlled India in the 17th century, and evolved to what we know it as today which is hot water poured over whiskey, usually paired with lemon juice and honey (via VinePair). There are endless variations of the hot toddy that include a variety of ingredients and spirits, including brandy, rum, or even aged tequila. 

If you want to add some additional winter flavors, try an apple cider hot toddy.  If you're starting with plain apple cider, consider heating it up in a pan along with brown sugar, cinnamon, ginger, and a cinnamon stick. The extra layers of sweet and spice will take your hot toddy to the next level.  

A lot of citrus fruit is at its peak in the fall/winter months, and luckily, the sweetness of bourbon paired with the acidity of the fruit is a pairing made for easy-to-sip cocktails. The Brown Derby is a good example of this combination that is elegant and timeless. The drink dates back to the Golden Age of Hollywood, as it was created in the 1930s at a Sunset Strip establishment called the Vendôme Club. However, it was actually named for a different Los Angeles restaurant, the Brown Derby, which was housed in a building shaped like a giant hat (via Quartz). 

A Brown Derby cocktail recipe is a balancing act of sweet, sour, and bitter. The key is to make honey syrup by combining honey and hot water so that it slightly dissolves so it sweetens the drink without being too thick. Then, you mix it with bourbon, grapefruit juice, and a citrus twist and you have yourself a mouthwatering drink. You can add a sprig of rosemary if you're feeling fancy, and squeeze in a bit of lemon juice for even more of an acidic kick.  

The distinct sweetness of maple just perfectly matches the flavors of the winter season. It's why it's the perfect addition to a bourbon smash, which is another example of bourbon and citrus pairing together perfectly. According to Chilled Magazine, a bourbon or whiskey smash is essentially the mash-up of a mint julep and a whiskey sour. The difference between a smash and a julep is the addition of fruit. (A sour features the addition of fruit, but it isn't muddled like this flavorful drink.) The origins of the whiskey smash are murky, but it's been a staple bar cocktail since the 19th century. 

You can make a bourbon smash using any fruit. During the summer, consider a strawberry and peppercorn combo or your choice of stonefruit. For the winter months, citrus is the way to go — the flavor of bourbon and maple pairs particularly well with muddled orange and lemons.

A Lion's Tail is one of the more advanced cocktails on this list — but it's well worth the effort. The drink is spicy, bitter, and robust as can be, like a more sophisticated version of the classic daiquiri. The complexity is contributed to the key ingredient in the drink: allspice dram. It's essentially a liqueur made out of light rum, allspice berries, water, cinnamon, and sugar that is added to many tiki-inspired cocktails. The Lion's Tail is also distinct for its use of bourbon and Angostura bitters, which add more depth to the drink. 

It's believed that the Lion's Tail was born out of Prohibition, even though the recipe was first published in "The Cafe Royal Cocktail Book" in London in the 1930s. The name of the cocktail is said to be a to reference the euphemism "twisting the lion's tail," which means to provoke the British (via Punch). 

Similarly to the Moscow Mule, a White Russian is a popular cocktail in the U.S. that has no origins in Russia. The drink is far from light, which is why its best-suited for cold-weather drinking. The traditional recipe features vodka, coffee liqueur, and cream. The Black Russian, which is the same cocktail without cream, was first made in Brussels in the late 1940s. Once the use of cream in cocktails was popularized in the 1950s, the heavy cream was added and the White Russian was born. Like the Moscow Mule, the name only helms from the base of vodka, which is often produced in Russia (via Chilled Magazine). 

To put a different spin on the drink, you can swap out or even add a shot of bourbon to the traditional recipe to make it even boozier. We suggest tracking down a bottle of 'Shmallow, a toasted marshmallow bourbon from Hotel Tango Distillery. When the sweet spirit is combined with vanilla vodka, coffee liqueur, and heavy cream it tastes like the boozy version of a s'mores in a glass. 

The old fashioned cocktail is the standard for bourbon drinkers. As the name suggests, it's been around seemingly forever. The whiskey-based drink was officially invented in Kentucky in the 1880s at a social club. Whiskey is combined with bitters, sugar, and citrus, usually an orange twist (via Thrillist). The classic recipe never goes out of style, but there are ways to tweak the recipe to make it even more suitable for the winter season. 

An easy way to make a Christmas version of an old fashioned is to muddle cranberries and sugar into the drink, which will help alleviate the tartness of the fruit. Add a sprig of rosemary for an herbal effect. For another fruity twist, consider an apple cider old fashioned which brings together bourbon, apple cider, black walnut bitters, toasted almond bitters, and a sugar cube, plus a thyme sprig for garnish. The result is a cocktail that tastes like apple pie with a boozy kick.

Hot chocolate is the official drink of the snowy season. It's as tasty as it is warming, so why not throw a little bourbon in it to amp up that entire experience? Hot chocolate is always better if you make it from scratch and it really doesn't take as much effort. It's not required to follow a recipe, though. You can just add as much bourbon as your heart (or alcohol tolerance) desires into your warm cup of hot chocolate. 

Some people may like their booze to taste more like dessert, so indulge your sweet tooth even more by adding a flavored spirit like Dough Ball cookie dough-flavored whiskey that pairs great with anything and everything chocolate. Of course, you can always add the traditional marshmallows to the equation. Top off with puffs (large or mini) or consider mixing marshmallow fluff directly in with the hot beverage.  

The Boulevardier is as sophisticated of a cocktail as it sounds. It also dates back to the Prohibition era, and was actually created at a bar in Paris frequented by American expats looking to get their booze fix (via Imbibe). It also happens to be Alton Brown's all-time favorite drink, which usually means it's one of those things that's so complex that it's good. It may not be as popular as an old fashioned, but it's a tried and true staple that's stood the test of time.

A Boulevardier is basically a Negroni that swaps bourbon for gin, meaning it's slightly sweet while still offering distinct notes of bitterness and spice. It features Italian liqueur, typically Campari, sweet vermouth, and a citrus twist. Most average bourbons will be a fine fit for the cocktail, but in our estimation, it happens to be one of the best cocktails made with Maker's Mark.

Eggnog is a drink that's really only appropriate to indulge in during the winter. To make it a cocktail worthy of holiday parties, just add a little bourbon to it. Eggnog isn't very difficult to make on your own. You'll need a lot of egg yolks and patience, as it needs to be cooked slowly and meticulously. Go ahead and make a big-batch recipe if you're planning on throwing a holiday party. It only takes basic ingredients like milk, heavy cream, eggs, sugar, and nutmeg to churn out this holiday treat, and it's one of those recipes that tastes better after it sits in the refrigerator for a bit. 

Coquito is a Puerto Rican holiday drink that's similar to spiked eggnog. Instead of eggs, coquito features coconut cream and milk. It also is typically made with rum. However, it would undoubtedly still be tasty, albeit not authentic, to make a batch with your favorite bourbon. 

It's a somewhat acquired taste to enjoy alcohol mixed with anything that is milk-based, especially for those people who aren't into dairy in general. That means the options for warm boozy drinks in the winter are limited, which is where spiked cider comes in. Hot apple cider is to be enjoyed the moment you feel a chill in the air. It's also ideal for parties because you can make a big batch of warm apple cider in a slow cooker for a crowd. 

The great thing about cider is there are plenty of ways to change up the recipe. You can add mix of spices such as peppercorns, allspice berries, cloves, and cinnamon or consider the addition of chai tea. To mix up the flavors, you can use a flavored bourbon like Knob Creek Smoked Maple or Jim Beam Kentucky Fire for some heat of the spice variety.  

Espresso martinis saw a massive resurgence in 2021 as the trendy combination of vodka and coffee fell back into fashion. The coffee-based cocktail has been around since the 1980s for partygoers to drink to both get them tipsy and wake them up (via Bourbon Banter). Now that the drink is popular yet again, bartenders have gotten creative with the different pairings of coffee and booze and that includes a simple syrup swap. 

Bourbon Banter suggests using the usual recipe of coffee liqueur, simple syrup, and espresso mixed with bourbon rather than vodka. The other unique aspect of the recipe is the addition of amaro, which is a bitter Italian liqueur that adds even more depth to the drink. However, you can just keep things simple with a combination of just bourbon, coffee liqueur, and espresso, especially if you don't enjoy a bitter bite when sipping your cocktail. 

The Paper Plane is a drink that serves as a refreshment and entertainment — that is, if it's properly garnished with a tiny folded paper airplane. The drink is one of the more recently-birthed cocktails on the list, as it was invented in 2008 at the Chicago bar The Violet Hour. Bartender Sam Ross named it after the M.I.A. song "Paper Planes." The original recipe contained bourbon, Campari, amaro, and lemon juice, but Ross decided it wasn't balanced. To subdue the bitterness, he swapped Campari for Aperol, which is the most common way it's now enjoyed (via Punch). 

The Paper Plane is like an elevated whiskey sour that was inspired by the popular Prohibition cocktail the Last Word, which pioneered the 1:1:1:1 ratio (via Wine Enthusiast). It's a simple recipe to make at home, with the hardest part truly being folding a perfectly portioned tiny plane to perch on the edge of the glass.

There are so many drinks with Collins in the name that the tall tumbler they're often served in is called a Collins glass. A Tom Collins is the most popular of the bunch, featuring gin, lemon juice, simple syrup, and club soda. The John Collins is similar, but swaps whiskey (or bourbon) for the gin and is often garnished with an orange slice and a cherry (via Bushmills). Even though the John Collins features whiskey now, that wasn't only the case

The John Collins was invented in London in the 19th century but featured the juniper-based genever spirit instead of its cousin gin. Then, Old Tom Gin was often used as a substitute in England, lending to the name Tom Collins (via The Online Wine Course). Now, if you order a John Collins, it should be a refreshing and bubbly version of the spirit with more of an earthy and warm flavor thanks to the addition of bourbon rather than herbal gin. 

A Manhattan is a cocktail as popular as an old fashioned, but it typically is made with rye whiskey rather than a corn-heavy bourbon. The simple recipe of whiskey, sweet vermouth, bitters, and a cherry also tastes great when swapping rye for bourbon, such as Woodford Reserve. Rye is typically peppery and the flavor can be overpowering, while bourbon is a more mellow and often sweeter version of whiskey. If you want the best of both whiskey and bourbon, you can use a high rye bourbon like Redemption High Rye bourbon that is spicy and sweet. 

As you might expect, the Manhattan is believed to have originated in New York in the late 1800s, even though the specific story of how it came to be and who first mixed the drink up are a mystery (via Difford's Guide). Regardless, it's another drink that has stood the test of time and is reputable for being sophisticated and always well-balanced if made correctly.