Bourbon Cocktails: 30 Of The Best

Finding specific fame in Kentucky, where it was first developed, bourbon has become synonymous with the cowboy image of the American Frontier, and remains an iconic beverage to this day. 

Bourbon is a popular choice amongst whiskey lovers and cocktail enthusiasts alike, famed for its smooth, drinkability when compared to world equivalents such as Scotch and Irish whisky, meaning it pairs well with most mixers and concoctions. 

1. The Manhattan

One of the most classic bourbon cocktails around, the Manhattan supposedly invented at The Manhattan Club in New York sometime in the 1870s. Whilst not verified, this is the most widely held belief as to its origins. 

Wherever it came from, the drink has become synonymous with the city, gaining particular popularity during the Roaring Twenties, when widespread prohibition throughout North America encouraged wild social rebellion. 

Although very much a nod to a bygone era in American history, the Manhattan remains widely popular to this day. 

2. Punch Flora

The punch flora is a subtle, sweet floral version of the classic punch, incorporating jasmine, cardamom and citrus. 

This is a great example of the versatility of bourbon, with simple ingredients turning into a light, refreshing summer drink. 

3. New York Sour

A unique twist on the classic whiskey sour, the New York sour transports you to a trendy Manhattan cocktail bar, mixing red wine, citrus bitters, and a whole lot of New York style. 

4. Bourbon Sidecar

Offering a twist on the classic brandy sidecar, the bourbon sidecar offers a much more drinkable, accessible taste for those who can’t stand the polarizing taste of brandy. 

With a heavy citrus flavor, and the after spice of the whiskey, this is somewhat similar to the classic whiskey sour, albeit trading the sourness for zesty, refreshing citrus. 

5. Classic Whiskey Sour

First published in Wisconsin newspaper Waukesha Plain Dealer in 1870, the whiskey sour is a staple of the cocktail scene.

Shaken and served straight up over ice, there are many variations of this cocktail, including the above mentioned New York sour, and the Boston Sour, which usually includes the inclusion of egg yolk. 

With a sour taste, as its name suggests, the whiskey sour is usually garnished with half an orange slice and a maraschino cherry. 

6. Bourbon Old Fashioned

Whilst a simple concoction, the Old Fashioned has similarly become a staple of the cocktail scene, offering drinkers a slug of bourbon whiskey, seasoned and sweetened with angostura bitters and sugar. 

Available in countless variations, this is a popular cocktail amongst whiskey lovers and cocktail enthusiasts alike. 

7. Old Fashioned Paloma

This variation on the classic Old Fashioned, the Old Fashioned Paloma takes inspiration from the classic tequila cocktail to create something completely different. 

Translating to ‘dove’, the Paloma takes the bourbon whiskey and combines it with lime juice and grapefruit flavored soda to create a refreshing fruit drink that is 100 miles away from it’s original namesake of the Old Fashioned. 

8. Maple-Bourbon Smash

Popularized by Robb Turner, the owner of Crown Maple, this twist on the classic Old Fashioned contains rich, sweet maple syrup and the finest bourbon whiskey to create a very seasonal, Autumn drink. 

9. Bourbon Limoncello

Combining a classic of modern America with a traditional Italian spirit liquor, the Bourbon limoncello represents everything good about the New World – namely the coming together of cultures and flavors to create something original and exciting. 

This drink perfectly combines the spicy, sweet, the sour, and the bitter, incorporating the zest and sharpness of the lemons, the sweetness of the sugar, the spice of the whiskey, and the bitterness of..

Well, the bitters, to create something refreshing, memorable and perfectly balanced. 

10. Bourbon Apple Cider Fizz

This cocktail gives drinkers the sweet, wholesome taste of apple pie, thanks to the tanginess of the apple cider, the spice of the ginger beer, and the sweetness of the sugar. 

Cocktail enthusiasts continue to push the boundaries of what a drink can be, and this is one example where they have taken something as polarizing as bourbon whiskey and made it completely warm, wholesome, and widely acceptable. 

It feels like a holiday staple, and after you have a taste, you won’t be able to wait for the fall, when you can light the bonfire, crack out some smores, and enjoy this fantastic slice of Americana. 

11. Blackberry Bourbon Smash

The main problem with standard bourbon whiskey, is that when the sun is out and the weather is warm, it isn’t really what you’d call a refreshing drink. 

With the blackberry bourbon smash though that could change, offering a sweet, refreshing fruit burst, laden with real blackberries and plenty of ice. 

Even the whiskey purists won’t be able to resist this fruity number. 

12. Bourbon Highball

This is a classic whiskey cocktail that is both simple, smooth, and delicious, offering a light, drinkable bourbon concoction without any fuss or muss. 

Available with both ginger ale and soda water, depending on your preference, the Highball is for the cocktail enthusiast who still likes to get a good taste of their bourbon. 

13. Bourbon Lemonade

Somewhat similar to the classic Highball, the bourbon lemonade takes the sweet, lightness of lemonade and combines it with tangy triple sec and the finest bourbon to create something subtle yet striking. 

14. Peach Bourbon Smash

The peach bourbon smash incorporates the gentle fruitiness of the peach, with the harshness of the bourbon to create something that is both tame and wild at the same time. 

Refreshing and perfect for those hot summer nights, the peach bourbon smash contains seasonal fruits, a hint of herbs to give it a playful spice, and the finest bourbon whiskey to give the glowing aftertaste to the whole shebang. 

15. Man O War Bourbon Cocktail

Named after one of the most famous race horses in history, the Man O War bourbon cocktail really packs a punch. 

Combining orange liqueur, lemon juice, sweet vermouth, and Kentucky bourbon – perhaps a nod to its horse racing origins – to create a sweet yet complex summer cocktail specifically designed with the fervor and animalism in mind. 

16. Whiskey Ginger & Lemon

Another classic amongst whiskey cocktails, this is a simple drink that almost anyone can easily produce at home. 

It’s as refreshing as it is simplistic, with just enough bite in the ginger ale to make you remember what a good time you had. 

17. Bourbon Eggnog

A popular seasonal beverage with a devilish twist, the bourbon eggnog offers the warmth and coziness of the holidays in one neat package. 

Laden with cinnamon and nutmeg, this really does taste like Christmas in a glass, and one or two of these will make your holidays a lot happier in no time at all. 

What you are getting is a wholesome dessert in liquid form, making you feel warm and fuzzy in all the right places. 

18. Kentucky Mule

Offering an American spin on the classic vodka cocktail, the Moscow mule, the Kentucky mule boasts a zingy lime finish paired with the highest quality bourbon. 

Simplistic, but with a spiced kick from the ginger beer, the Kentucky mule lives up to its name, offering a hardy, enjoyable drink with just a dash of excitement. 

19. The Little Italy

Created by Audrey Saunders of the Pegu Club Bar in New York City, the Little Italy is essentially a classic Manhattan with campari and angostura bitters. 

Originally made with rye whiskey, bourbon equivalents have become ever more popular, due to the wider availability of bourbon whiskey in bars and clubs. 

A tasteful cocktail with just enough excitement to stand out from the crowd, the Little Italy pays tribute to its Italian American roots while waving the flag of individuality. 

20. Cranberry Orange Bourbon Cocktail

A great all rounder cocktail, the cranberry orange bourbon is great for both festive winter gatherings, and summer get-togethers, thanks to the versatility and fruitiness of the cranberry and orange pairing. 

Topped off with sparkling water for those few extra bubbles, this is a light and playful take on classic whiskey cocktails, offering a camp and fun addition to the wide repertoire of bourbon smashes. 

21. Old Fashioned Maple Brown Derby

A modern take on the classic Brown Derby, created at Los Angeles’ Vendome Club in 1930, and named after the Brown Derby-shaped hat store of the same name, the Maple Brown Derby gives the spice and the sourness of this Hollywood classic, with the rich, sticky textures of classic North American maple syrup. 

This makes for an unusual yet attractive combination, one as complex and mysterious as the era the original was created in.

The finished product is a modern classic, and one that will quickly become a go-to cocktail when you are in the mood for a little bit of Hollywood pizzaz. 

22. Sweet & Spicy Bourbon Cocktail

This is a somewhat unusual summer cocktail, combining the fire of a classic bourbon, with the sweetness of mixed summer fruits, and the spiciness of jalapeno chilis. 

It shouldn’t work, but the actual result is something that cannot be ignored.

Fiery and lovely in all the right places, and with a complexity to the flavor that leaves you wanting more, the sweet & spicy might not be for the faint of heart, but those brave enough to give it a try will never look back. 

23. Amaretto Old Fashioned

If the Old Fashioned wasn’t classically cool enough, then the Amaretto Old Fashioned should provide you with enough style, substance, and intrigue to keep you going all night. 

With a foundation of Amaretto cherry liqueur, combined with bourbon, maraschino cherry juice, and the light fizz of 7-Up, this drink is anything but ‘old fashioned’, taking you on a complex journey into the heart of true flavor. 

24. Toasted Pecan Old Fashioned

If there was one drink that properly summed up the great outdoors of North America, then this might just be the one. 

With toasted American pecans, that sweet molasses taste of brown demerara sugar, and pecan infused bourbon, this Old Fashioned feels very much like a fitting tribute to the country that bore it. 

25. Bourbon Pumpkin Smash

A quintessential fall drink, the bourbon pumpkin smash gives that perfect warm, cozy feeling, with pumpkin spice syrup, bourbon whiskey, and a bubbly texture, making it the perfect choice for seasonal family get-togethers and parties. 

If a cozy, winter Hallmark card could be boiled down into a single drink, it would be this, offering the equivalent of a warm woolen sweater and a roaring fire. 

Taking inspiration from the pumpkin spiced lattes popularized by modern coffee shop culture, bourbon pumpkin smash is a contemporary classic that looks as though it is here to stay. 

26. Boulevardier

As some of you may know, the Boulevardier is a bourbon alternative to the classic Negroni, replacing the gin with the finest of American whiskey. 

With sweet vermouth and campari, the Boulevardier is a simple yet stylish drink, and an interesting take on a piece of mixology history. 

27. Mint Julep

A drink with a long association with the Kentucky Derby, the Mint Julep takes mint leaves, angostura bitters, and sugar syrup, and combines it with the fiery taste of Kentucky bourbon to create something as opulent yet wild as the races themselves. 

28. Rooster Cocktail

Named for the famed John Wayne character ‘Rooster Cockburn’, this too feels like an American classic straight out of the Old West, combining sarsaparilla and bourbon whiskey to deliver a spiced, complex combination of flavors. 

Combined with a cinnamon liqueur, this brings both the flavors together, and a little salt around the rim gives it just the right amount of ‘True Grit’. 

29. Paper Plane

Featuring bourbon whiskey, Aperol liqueur, amaro, and lemon juice, this cocktail has a bittersweet flavor palette, with the underlying character of the bourbon and zestiness of the lemons shining through to give it a great aftertaste. 

Don’t let its whimsical name fool you, this whiskey cocktail packs one hell of a punch!

30. Boilermaker

And finally, something gritty and classic to take bourbon back to its roots. 

For fans of bourbon and beer, this is the perfect combination, and while its classification as a cocktail could be argued until the cows come home, its reputation and legend make it worthy of a place amongst these alcoholic contenders. 

Originating in Butte, Montana in the 1890s, the drink was originally called a ‘Sean O’Farrell’, and commonly served to miners at the end of their shift.

Commonly served separately – as a ¾ glass of beer and a whiskey shot – they can either be drunk separately (as a beer and a shot), or together by dropping the shot into the beer, and consuming as one. 

But however you consume it, this beer cocktail is a great example of working-class American culture that has stood the test of time and become something of a legend amongst mixologists and customers alike. 

Frequently Asked Questions

Can Bourbon Be A ‘Summer Drink’?

Absolutely! While in the past it might have been reserved for dingy barrooms and thoughtful brooding, bourbon can now be paired with numerous mixers and fruit combinations to give it a fizzy, light feel perfect for daytime summer consumption. 

What Mixers Can Bourbon Be Paired With?

This depends on the kind of drink you are hoping to create, and of course your personal taste, but generally bourbon can be paired with ginger beer, tonic water, soda water, lemon juice, fruit liqueur, and even Coca-Cola. 

Ultimately it is down to your personal taste, and if you like to drink something, then how can it possibly be ‘wrong’?

How Versatile Is Bourbon? 

As this list perfectly illustrates, bourbon can be far more versatile in cocktails than its reputation suggests. 

Is Bourbon Expensive?

There is an entire range of differently priced brands, all of which bring something a little different to the table. 

However, you don’t need a top shelf bourbon to make a good whiskey cocktail, and there are plenty of mid-range products on the market that both taste great and offer a wide range of options. 

Final Thoughts

And there we have it, everything you need to know about bourbon cocktails, and some of the best options out there. 

There is a whole world of possibilities with bourbon whiskey, and regardless of what the occasion is, you can always find the perfect cocktail to fit the bill. 

Why not try some? Just remember, drink responsibly!