14 Easy Bourbon Cocktails for Every Occasion (Including a Tuesday)

Bourbon. It’s a timeless drink, and one of the most versatile there is.

Typically enjoyed neat, the best way to add a layer of finesse and class to your bourbon is to mix in a few other flavors and make one of the many bourbon cocktails that have sprung up over time.

Whether you’re out on a date, at the blues club, or even having a night in by the fire on a Tuesday (yes, a Tuesday!), this list has you covered for every type of bourbon cocktail you could ever need.

The Best Bourbon Cocktails

1. Old Fashioned

Let’s start with the godfather of bourbon cocktails. The number 1. The standard. It’s the whiskey Old Fashioned.

Simply dash some Angostura bitters into your bourbon and add some sugar syrup and you’ll be sipping on a drink enjoyed by millions looking and feeling like the big cheese.

For extra flair, garnish your tumbler with a lemon twist (make sure to light it to release all those hidden flavors). This cocktail is packed with history, it’s been called the Old Fashioned since at least the 1930s, referring to how cocktails were made pre prohibition.

No bourbon drinker can truly pass this one up. That brilliant mix of sugar, bitters, and whiskey has passed many lips before yours and will continue to pass through many after, don’t miss out on it. 

2. Manhattan

The perfect blend of Italian and American, you can imagine Al Capone sipping one of these, cigar in hand, in one of New York’s most exclusive speakeasies. You can’t get any cooler.

An ounce of sweet vermouth and 2 dashes of angostura bitters stirred into 2 ounces of your favorite bourbon, and served in a coupe with a cherry, will give you a staple of any good cocktail menu.

In 1882, the Democrat Newspaper quipped ‘it is but a short time ago that a mixture of whiskey, vermouth, and bitters came into vogue, and guess what? It’s never fallen out of fashion.

Before you rush off into all the fancy and out there bourbon drinks you can make (and trust us, there are many), make sure you’ve tried a good Manhattan. 

3. Bourbon Sour

An incredible, versatile drink with plenty of variations to play around with, no list of the best bourbon drinks would be complete without the iconic whiskey sour.

2 ounces of bourbon, ¾ ounce of freshly squeezed lemon juice, then a ½ ounce each of simple syrup and egg white to your shaker, shake and strain into a rocks glass and the quintessential bourbon cocktail is ready to drink. 

4. Mint Julep

It’s impossible to think of this cocktail without thinking of Sean Connery’s James Bond enjoying it with his arch nemesis Goldfinger.

The Mint Julep whispers sophistication, class, and style. It’s a brilliantly simple one to make. Just muddle some mint leaves and a brown sugar cube in the bottom of a highball, pack tightly with crushed ice and pour over 2 ounces of your favorite bourbon.

Garnish with a sprig of mint leaves and you’ll be feeling like an MI6 agent in no time!

5. Highball

If you’re looking for simplicity, look no further. Whiskey, soda, ice. 3 ingredients to make up one of the most refreshing ways you can enjoy a bourbon.

A dash of elderflower cordial will add a totally new twist to this classic if you’re feeling a touch adventurous.

Just remember to build this one over ice and give it a stir, no shaking up your bourbon and ice before adding your soda water. 

6. Brown Derby

A hark back to the golden age of Hollywood, a slightly obscure mix of bourbon, grapefruit juice, and honey syrup is nonetheless a joy to the taste. A simple shake and strain recipe, the brown derby is best balanced with 2 ounces of bourbon, 1 ounce of grapefruit juice, and ½ ounce of honey syrup, garnished with a grapefruit wedge.

The sweetness of the honey will balance out the tartness of the grapefruit and leave you with a lovely classic that’s currently enjoying its renaissance within the cocktail community. 

7. Hot Toddy

Perfect for an afternoon drink after a day on the ski slopes, the Hot Toddy goes back centuries.

Add a couple of teaspoons of lemon juice and honey to a mug of boiling hot water, stir in 1 ½ ounces of bourbon and garnish with a lemon wheel and cinnamon stick and you’ve got the perfect remedy for the winter chills. 

8. Bourbon and Coke

Another perfect example of simplicity being a bourbon cocktail’s biggest strength, the bourbon and coke is most people’s introduction to whiskey.

Built over ice, this classic bourbon drink works well with any bourbon of choice and adds a nice, sugary fizz to an otherwise strong and smooth spirit. 

9. Kentucky Mule

Aptly named for a drink that packs a hell of a kick, the Kentucky Mule is an absolute must on any bourbon lover’s list.

½ an ounce of fresh lime juice squeezed into 2 ounces of bourbon, filled with ice, and topped with ginger beer brings out an aggressive, spicy flavor not to be taken lightly. Garnish this one with a mint sprig and lime wedge to give yourself maximum punch from this hard classic. 

10. Boulevardier

Whiskey’s answer to a negroni, the boulevardier is a brilliant aperitivo drink fit for lazy summer afternoons before a nice late dinner.

Equal parts bourbon, vermouth, and Campari bitters make for a brilliantly strong, sweet concoction best enjoyed socially either before or after a meal. Make sure to keep your measures equal, as this is a bourbon cocktail that relies on the delicate balance of all its different flavors so just build over ice, give it a gentle stir and garnish with an orange twist before you don your best linen shirt and sip this one into the sunset. 

11. Gold Rush

If you want to feel like an outlaw, a renegade, a lone ranger, then look no further than the wild west inspired Gold Rush.

2 ounces of bourbon combined with 1 ounce each of honey syrup and lemon juice should be shaken and strained into a rocks glass and enjoyed with a lemon twist garnish.

A few sips of this easy bourbon cocktail and you’ll be feeling like Clint Eastwood in absolutely no time. 

12. Paper Plane

In a list packed to the rafters full of classics, the Paper Plane is the new kid on the block.

The original 2008 recipe calls for ¾ ounces of bourbon, Aperol, freshly squeezed lemon juice, and amaro nonino quintessentia (an Italian bitter liqueur), shaken and strained into a coupe glass. If you’ve never heard of amaro nonino quintessentia, or have absolutely no idea how to get hold of it, don’t worry.

Either angostura bitters or vermouth will work as a substitute, keeping the drink’s Italian edge and bitter flavors. If you’ve never tried (or even heard of) a paper plane, give it a go.

You’ll be blown away by the excellent combination of flavors that is sending this drink on a one-way street to becoming a modern classic!

13. Maple Old Fashioned

Similar to its older brother, the maple old-fashioned simply swaps out the simple sugar syrup for Canadian maple syrup. It may seem like quite a basic change, but the maple old fashioned takes on a much heavier flavor than its basic counterpart.

Most of your favorite bourbons are either going to have maple notes or notes that pair well such as oak or honey, making the maple old fashioned a surprisingly easy twist on a bonafide classic.

Some purists may turn their nose up at it, but there’s absolutely no reason for you to when it tastes as good as it does!

14. Sidecar

Confession time: this isn’t normally a whiskey cocktail.

The sidecar is synonymous with cognac, a French brandy.

However, swap that out for bourbon and you’ve got a potent mix fully capable of knocking your socks off.

Best balanced in a 2:1:1 ratio, I’d recommend starting off with 1 ½ ounces of bourbon, ¾ ounce of orange liqueur (Cointreau is going to be your best value and most accessible bet here), and ¾ ounce of freshly squeezed lemon juice.

Shake and strain into a sugar-rimmed coupe glass and garnish with an orange twist and you’ve got a brilliantly American take on a French standard.

If you want to stay truly authentic to the history of this brilliant cocktail, strain the leftovers from the shaker into a shot glass. That’s right, it’s actually the shot of leftovers that is the original sidecar, not the drink itself!

Conclusion

There you go!

14 brilliant bourbon drinks to not only get you started but deep into the world of shaken or stirred summer whiskey cocktails.

If you’re not sure where to start, definitely begin with the old fashioned and manhattan.

They’re the heavyweights in the bourbon cocktail game and they’re on every half-decent cocktail menu in the country for good reason. They taste great and appeal to a wide range of palates due to their brilliantly balanced flavors.

The only thing left now is to pick your bourbon. Luckily, we aren’t hanging you out to dry with this either. Be sure to read our best bourbons for an old-fashioned article and we’ll cover all the bases for you to get started on your bourbon cocktail adventure!