There’s nothing better than sitting back and relaxing with a good drink, especially surrounded by your loved ones.

Bourbon is an incredible liquor to sip, but the oak, caramel, and vanilla notes are easily enhanced by simple syrups, bitters, lemon juice, and more to create perfectly balanced cocktails.
To my fellow bourbon lovers — I’ve compiled a list of some of the best bourbon cocktails around that are must-tries.
The best part about many of these drinks is that they’re customizable, and you can play with the ingredients and ratios to craft your perfect drink. Don’t be afraid to experiment! You might find your new favorite drink.
Check out the list below to find a new drink (or drinks) to make at your next gathering. Always drink responsibly and enjoy.
Now onto the cocktails!
Boulevardier
Erskine Gwynne was onto something when he first created this drink.
The Boulevardier is for the bold. Soft notes of vanilla, oak, and caramel from the bourbon combine with the strong, bittersweetness of Campari and the sweet vermouth for a drink that’ll keep you warm on those chilly fall and winter nights.
This drink is based loosely on the Negroni and includes ⅓ bourbon, ⅓ Campari, and ⅓ vermouth with an orange garnish.
I prefer to make my Boulevardier with a slightly higher proportion of bourbon, so it cuts nicely through the bitter Campari and rich vermouth.
I love to whip one of these up and sit around the bonfire during the fall time or in front of a fireplace on those snowy winter nights.
Bourbon Sidecar
The original Sidecar is thought to have been invented around the end of World War I, in either London or Paris.
It was originally made with cognac or Armagnac but has since been modernized with delicious, oaky bourbon.
If you’re a fan of sour drinks, the Bourbon Sidecar is right up your alley! You’ll enjoy hints of sweet citrus mixed with caramel, vanilla, and toasty oak aromas.
The classic Bourbon Sidecar recipe consists of bourbon, Cointreau, and lemon juice, but there are many variations you can try, depending on your preferences.
My favorite way to make this drink is to combine bourbon, Cointreau, lemon juice, and a tiny bit of simple syrup in a shaker and go to town. Strain into a glass and garnish with a lemon or orange twist or peel.
Mint Julep
The Mint Julep has been known as the official drink of the Kentucky Derby since the 80s, but its origins lie in the Middle East.
It started as a medicinal mixture called “Gulab,” which means rosewater. Later, the mixture made its way to the US, and the Mint Julep was born.
Early versions of the drink were made with brandy, cognac, or rum, depending on where you lived.
Today, the Mint Julep is a refreshing drink crafted with bourbon, sugar or simple syrup, and mint.
This cocktail is your perfect drink if you enjoy the oaky taste of bourbon with a hint of sweetness and the crispness of mint.
Black Demure
The Black Demure was invented by New York bartender Franky Marshall and is typically made with Wild Turkey 81-proof bourbon, but you can substitute your favorite bourbon.
This drink combines bourbon, triple sec/Cointreau, creme de mure, lemon juice, and simple syrup to create the best blackberry sour you’ve ever had.
The prominent blackberry flavor is highlighted by the lemon and bourbon.
There’s no better drink to sip during the summer than the Black Demure, and if you’re a fan of blackberry, this is the cocktail to make at your next outdoor gathering.
Bourbon Eggnog
Nog lovers rejoice! ‘Tis the season for a delicious drink.
But this drink isn’t specific to Christmas time; if you’ve got bourbon and eggnog, you can whip up this creamy, spiced cocktail any time you like.
The full-bodied cinnamon and nutmeg combine with the smoky, sweet taste of bourbon and the richness of the eggnog for the perfect spiced taste.
The drink is highly customizable. You can opt to make homemade eggnog for a personal touch or simply buy it from the store in season.
Either way, this drink will have you feeling extra warm and cozy on those crisp fall and winter evenings.
Ginger Rabbit
The name of this drink is appropriate because, after a few Ginger Rabbits, you’ll surely be hopping.
Damian Windsor pioneered this spicy-sweet concoction by combining:
- Black tea
- Star anise-infused simple syrup
- Fresh ginger
- Bourbon
- Creme Yvette
Creating the simple syrup is easy; add one black tea bag to 12 ounces of warm simple syrup and let it sit for 12 minutes.
Discard the tea bag, lightly crush six star anise pods and add them to the container. Let it stand for 24 hours, and then you’re good to go!
I love all things spiced, so this drink is one of my favorites. The Ginger Rabbit is like a boozy spin on a spiced, iced Chai — perfect for fall and winter.
Gold Rush
The Gold Rush is a simple, three-ingredient cocktail bursting with flavor.
It’s made with a slightly aged bourbon (four to eight years is the sweet spot — too old, and you risk the heavy oak taste dominating the drink), honey, and lemon juice.
Instead of plopping honey directly into your glass, try creating honey syrup using a 1:1 ratio with sugar.
You can add a little water to it if you want it looser. I prefer this method because it allows the honey to mix fully into the drink, and you’re not left with globs in the bottom of your glass.
Kentucky Mule
The Moscow Mule is one of the most popular drinks around.
But the name refers to the use of ginger beer in the cocktail, so there are many variations of the drink.
The Kentucky Mule uses bourbon instead of vodka and combines it with ginger beer for a robust flavor that will light your tastebuds up.
I like my drinks a little zestier and opt for the spiciest ginger beer I can find, so it meshes well with the strong profile of the bourbon.
Another alternative is to create your own ginger simple syrup and use club soda as a topper.
Manhattan
The Manhattan is a drink not very creative in name, but one that’s known far and wide.
This drink was thought to have been created in Manhattan in the 1880s and has stepped in and out of the limelight until it became a craft cocktail classic.
Bourbon and Italian vermouth meet to combine with a few dashes of fragrant bitters for this tasty and timeless drink.
Depending on your taste, you can use half sweet and half dry vermouth for a perfect blend or vary the ratios to highlight the flavor of the vermouth over the bourbon.
The classic ratio is two parts whiskey, one part sweet vermouth and bitters — stirred, never shaken — and topped with a candied cherry. However you take it, you can’t go wrong with this bourbon staple.
New York Sour
New York was the place to be when all these delicious cocktails were crafted.
If you’re a fan of red wine and sour drinks, you’ll love this rich, tangy concoction. The New York Sour has the same base recipe as a classic Whiskey Sour:
- Bourbon
- Lemon juice
- Simple syrup
- Egg white
But it has a twist; after you’ve combined all the ingredients into the shaker and strained it into a glass, you’ll take one-half ounce of red wine and pour it over the back of a spoon onto the drink so it floats on top.
You’re left with a beautiful, sour, and rich cocktail that you can sip all night. As an avid wine drinker and all-things-sour lover, this is one of the best bourbon cocktails on the list.
Old Fashioned
The Old Fashioned — I’ve heard this drink referred to too many times as an “old man” drink.
I am certainly not an old man, and that is not the case. This striking cocktail is for anyone who loves bourbon with a touch of bitterness!
It’s critical to choose high-quality bourbon for this drink. If you wouldn’t sip on the bourbon alone, it’s not the one; now’s not the time to be cheap.
Once you have your bourbon, you can decide if you want to use simple syrup or muddled sugar.
Simple syrup will save you some time, but if you want an Old Fashioned similar to the drink they had in the 19th century, grab some sugar cubes.
If I have time, I like to make it with muddled sugar or cubes. If I’m in a hurry (or just feeling lazy), I’ll bring out my simple syrup. As long as your bourbon is high-quality, you have some flexibility.
The Bourbon Sour
Don’t let the classic name of this cocktail fool you. The Bourbon Sour may be a simple drink, but it still packs a mean punch in the flavor department.
The oaky, caramel, vanilla notes of the bourbon mixed with an acid (lemon) and sugar deliver a tangy, punchy taste that’ll have your tongue tingling.
You’ll need two ounces of your favorite bourbon, one ounce each of fresh lemon juice and simple syrup, and an egg white. Grab some sliced oranges and cherries to garnish and enjoy.
Again, I love all things sour, so this drink is always a go-to for me. I drink it year-round, but I especially love to sit around a barbeque or a bonfire and sip this masterpiece.
The John Collins Cocktail
The John Collins Cocktail is thought to have been created in the 1800s by a headwaiter in London, becoming a distinct version of the Tom Collins cocktail.
Today, there are many spin-offs in the Collins drink family.
The recipe is similar to bases for other bourbon cocktails, with a couple of ounces of bourbon, freshly-squeezed lemon juice, simple syrup, and club soda.
This cocktail is a crisp drink for any summer get-togethers and is a perfect go-to when you’re not sure what to have. It’s light and packed with flavor.
Whiskey Smash
If you liked the Mint Julep, say hello to its fruity 19th-century cousin.
You’ll need a good muddler for this recipe; luckily, they’re not very expensive. This drink consists of lemon wedges, bourbon, simple syrup, and mint leaves.
Use the muddler to compress the lemon wedges and release the oil from the peel. That oil is what gives the drink a richer taste when combined with the whisky and sugar.
The Whiskey Smash is another good outdoor summer drink, but it’s good year-round. I love to whip these up at barbeques!
Revolver
For my caffeine lovers, get ready for this drink! The Revolver is a deliciously caffeinated twist on the classic Manhattan and uses coffee liqueur instead of sweet vermouth.
This drink is easy to make with only three ingredients: bourbon, coffee liqueur, and orange bitters.
Topped with a flamed orange peel, this drink will have you feeling warm and wide awake.
It’s perfect for those chilly fall nights around the bonfire or at Christmastime sitting in front of the fireplace.
This cocktail is one of my favorites because it’s super simple, but it packs a punch in the flavor department!