Chocolate Old Fashioned Cocktail

April 6, 2021

An old fashioned, to me, is the perfect blank slate for cocktail creation. It’s delicious in its simplicity and its versatility. In fact, I’d say that an old fashioned is one of the few cocktails that you really can’t make incorrectly. As long as there’s bourbon and bitters somewhere, I’m good. This version is a chocolate old fashioned, which brings in a sweet element that helps kick new life into this classic.

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Sometimes when I develop recipes, I’m all about new flavor combinations. But in this case, I didn’t have to stretch too far. I already know that chocolate pairs excellently with bourbon, cherry, and orange each on their own. And those just happen to be the three main flavors in a standard old fashioned cocktail.

It was pretty easy to make this work well with the chocolate flavor, and I think you’ll find that it does an excellent job of highlighting the cherry bitters and cocktail cherries. The result is something just sweet enough, but that you are still able to sip on all night, if you’d like. Plus, it’s just super gorgeous with those drips.

What You Need to Get Started

You can easily find all of the ingredients for these chocolate old fashioned cocktails at your grocery and liquor stores:

Let’s Make a Chocolate Old Fashioned

Cocktails come together pretty quickly in most cases, and this one is no exception. To get started, gather all of your ingredients. If you are making a few of these drinks at a time, I find it easiest to do this assembly line-style. Do each step for all the glasses, then move on to the next step.

To get started, add a sugar cube to a rocks or double old fashioned glass. Something with a thick base is best, since we’ll be muddling. But if you don’t have glasses specifically for cocktails, a standard low-ball water glass is fine.

Add a couple dashes of both types of bitters (or drops, if your bitters came with a dropper instead) onto the sugar cube. In a standard old fashioned, you would use an orange peel and cherries as garnish. Here, we are bringing in those flavors through the two different types of bitters.

The bitters aren’t quite enough liquid to saturate the sugar cube, so add a little bit of water into the glass as well. Then use your muddler to break down the sugar cube and combine everything together.

Now, you may be wondering why I suggest doing this before adding the chocolate drizzle. Well, if you’re anything like me, you’d probably get both your hands and muddler covered in chocolate if you swapped these steps. But feel free to give it a try!

To get that nice drippy drizzle, use the chocolate syrup bottle to basically trace the rim of the glass, erring toward the inside. If you get a little bit on the outside, it’s fine. You can wipe it off (or lick it off, if it’s your own glass). Any time you pause, you will get a slight drip, but you can also go back and add these by just squeezing a little extra syrup at one point, and then letting the excess drip down.

Now, add a giant ice cube to the glass. If you don’t have a giant ice cube tray, you can use a few standard ice cubes instead. However, these will melt faster and create a more diluted drink sooner. In some cases, that may be what you are going for, especially if you are not used to drinking nearly straight liquor.

Speaking of liquor, let’s go ahead and add that in. First add the dark chocolate liqueur (or creme de cacao). Be sure you are using a dark version, which is not creamy and doesn’t contain dairy. The creamier milk chocolate liqueur will cloud your drink and be less chocolatey in flavor.

Next add in the bourbon. My favorite is Maker’s Mark, which has a sweet and syrupy flavor profile. However, if you have a favorite that you keep on hand, go ahead and use that. With drinks like this, it can be fun to try a few different variations with different bourbons, since you can really taste the flavor of it.

Finally, garnish the drink with a few cocktail cherries on a skewer. If you don’t have skewers, it’s totally fine to just toss the cherries in the glass. I love it when they sit in the drink until the end, soaking up all the alcohol. Then you basically get the eat some drunken cherries for dessert!

Cocktail cherries can be a little confusing if you are not familiar. They are sometimes called maraschino cherries, under the brand Luxardo. These are Italian maraschino, and not the same as the bright red cherries (American maraschino) you’d put on an ice cream sundae.

Instead, cocktail cherries are generally darker and less sugary. If all you have is ice cream sundae cherries, try them out. However, your drink may be a bit sweeter as a result.

Upgrade your classic favorite drink with a chocolate twist! This chocolate old fashioned is the perfect way to treat yourself with a sweet yet super sippable cocktail.

How to Serve a Chocolate Old Fashioned

This cocktail is perfect to serve for happy hour or as a before dinner drink. If you are looking for something similar but without the chocolate, try an amaretto old fashioned instead.

You could also use this to add a fun sweetness to brunch. Serve it alongside a fresh cherry cobbler to really highlight cherry season, or cocoa cinnamon rolls to feature the chocolate. For something a bit different, try a chocolate old fashioned with a savory caramelized onion cheesecake.

Of course, the chocolate definitely lends itself to dessert. Try it paired with a couple scoops of coffee ice cream for a bit of flavor contrast. You can also play up the chocolate with rocky road black bean brownies. For a little bit of both, you can’t go wrong with cherry chocolate chip cookies.

Use Up Leftover Ingredients

Chocolate old fashioned cocktail with spoon
Print Recipe
5 from 4 votes

Chocolate Old Fashioned

Upgrade your old fashioned cocktail with a chocolate twist! Dark chocolate liqueur and a syrup drizzled glass modernize and sweeten up this classic.
Prep Time5 mins
Cook Time0 mins
Total Time5 mins
Course: Drinks
Cuisine: American
Servings: 1 cocktail
Calories: 281kcal

Ingredients

  • 1 Sugar cube
  • 2 dashes Cherry Bitters
  • 2 dashes Orange Bitters
  • ¼ oz Water
  • 1 oz Dark Chocolate Liqueur
  • 1 ½ oz Bourbon
  • ½-1 tsp Chocolate syrup for drizzling
  • 3 Cocktail cherries for garnish

Instructions

  • Place the sugar cube in the bottom of a rocks or doubled old fashioned glass. Add a few dashes of each type of bitters on top of the sugar cube, and then saturate with the water. Muddle until the cube is broken down and the sugar just begins to dissolve.
  • Squeeze the chocolate syrup bottle around the inside rim of the glass, pausing at certain points to create larger "drips" down the side. Add the large ice cube into each glass.
  • Add in the dark chocolate liqueur and bourbon. Use a bar spoon to stir gently until combined.
  • Garnish with 3 cocktail cherries on a skewer and serve immediately.

Notes

  • Cocktail cherries are sometimes called maraschino cherries, under the brand Luxardo. These are not the same as the bright red cherries you'd put on an ice cream sundae. Instead, cocktail cherries are generally darker and less sugary. 
  • For a non-alcoholic version: Mix 1 tbsp + 2 tsp water with 1 tsp chocolate extract or chocolate syrup to replace the dark chocolate liqueur. Use an alcohol-free whiskey to replace the bourbon. Double check your bitters do not contain alcohol, as some brands do.
  • Other alternatives:
    • Replace the chocolate liqueur with coffee liqueur or kahlua for a mocha flavor. 
    • Garnish with a chocolate orange wedge or a chocolate covered cherry for more decadence.
    • For a more prominent orange flavor, muddle a piece of orange peel with the sugar cube, and leave it in the glass.
    • If you don't have a giant ice cube tray, or prefer a more diluted drink, you can use 3-4 standard ice cubes. These will melt faster.
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13 thoughts on “Chocolate Old Fashioned Cocktail

  1. Well, this is another one I definitely have to try! I like bourbon best out of the “whiskey family” and we actually spent Easter at our local distillery this year for something different. I have a number of these ingredients on hand. I bought the “Fancy” cherries instead of the bright red ones about two weeks ago for cocktails haha. The only thing I really need is flavored bitters – I didn’t even realize they had different flavored ones (though I shouldn’t be surprised) !

  2. I’ve never heard of a chocolate cocktail, and this one looks amazing and delicious! I need to write down these ingredients and make this for my brothers! 🙂

  3. My husband enjoys a glass of bourbon on ice from time to time, but I prefer mine mixed. I can totally get on board with this cocktail. It really does look so pretty with the chocolate drizzle. Thanks for making my bar list even longer, Kait! 😉

  4. I love the pictures! The chocolate drizzled around the cup is a nice touch. An Old Fashioned is one of my favourite drinks, so I’ll have to give this a try!

  5. I’m not usually much of a cocktail girl, but you had me hooked with the chocolate AND how pretty the drink is! I’m totally intrigued to try this now!

  6. This combination is perfection; chocolate paired with bourbon, cherry and orange. The Amaretto variation sound absolutely amazing too, can’t wait to try it.

  7. This was an immediate pin for me because I absolutely adore an Old Fashioned and this is such a creative twist! I don’t typically *love* chocolate, since it can tend to be too sweet for me, but I think with the flavors of an Old Fashioned, it would be a perfect dessert beverage! I seriously can’t wait to try this!

  8. How have I not tried one of these before?! Chocolate and cherries, yes please! I think this is the perfect drink for a cozy night or something special 🙂

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