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Cherry & Chocolate Old Fashioned Cocktail

A twist on the traditional old fashioned cocktail made with black cherry whiskey, chocolate bitters, cherries, a sugar cube, and a fresh orange peel. Served on the rocks and ready for sippin’. It’s smooth and sweet while still staying true to its classic roots. 

A cherry and chocolate old fashioned cocktail.

I had an old fashioned at the Junction 35 Distillery in Gatlinburg, Tennessee. It became the inspiration for this cherry and chocolate old fashioned. It’s delicious when made with their black cherry whiskey. But you can use your favorite cherry whiskey.

If you find yourself in Gatlinburg, stop by Junction 35. The food is delicious. And you can buy a bottle of black cherry whiskey to bring home!

This modified old fashioned uses cherry whiskey and chocolate bitters to give it a unique taste. Let’s be clear here. This is still a proper old fashioned cocktail. The chocolate and fruity notes are smooth and sweet but not overpowering. I’ve seen folks add chocolate syrup, creme de cacao, and even melted candy bars to drinks and try to pass them off as an old fashioned. That may be tasty, but it is something else entirely. 

Don’t worry. You can drink this chocolate and cherry old fashioned and feel like a dignified lady or gentleman.


Black cherry whiskey, chocolate bitters, sugar cubes, bourbon cherries, an orange, a large cube of ice, and an orange zester.
  • Black Cherry Whiskey. I like the Black Cherry Tennessee Whiskey from Junction 35 Distillery in Tennessee. You can use Jim Beam Red Stag Kentucky Bourbon or your favorite black cherry whiskey. 
  • Chocolate Bitters give this old fashioned a hint of chocolate that adds depth of flavor. If you can’t find them locally, they are easy to order online. Fee Brothers Aztec Chocolate Bitters are the best I’ve tried. You can also use Angostura Cocoa Bitters or Woodford Reserve Chocolate Bitters.
  • A single sugar cube adds sweetness to the drink, and using them to make cocktails feels classy. 🙂 If you don’t have a sugar cube, use 1 teaspoon of simple syrup or 1 teaspoon of sugar.
  • A cocktail cherry gets muddled into the drink, and you’ll use 1 or 2 more for garnish. Use regular maraschino cherries, Luxardo cherries, or bourbon-soaked cherries.
  • Fresh orange peel adds an aromatic touch of citrus. It complements the chocolate, cherries, and whiskey and looks fancy as a garnish.
  • Ice chills the cocktail and adds a bit of water as it melts. You want to use large pieces of ice in an old fashioned rather than small or crushed ice.

Equipment Needed

You’ll need a channel knife or a paring knife to peel the orange. You’ll also need a muddler, a rocks glass, and a stirring spoon.

How to Make a Cherry and Chocolate Old Fashioned

A twist of fresh orange peel.

Use a channel knife to cut a ribbon of fresh orange peel. If you don’t have a channel knife, use a paring knife to cut a piece of the peel.

Place a cherry and a sugar cube in the bottom of a rocks glass. Then dash the bitters on top. Muddle them gently. Then, add a large cube of ice or several regular-sized cubes. Don’t use crushed ice!

Pour the whiskey on top, add the orange peel, and give it a brief stir.

A cherry and chocolate old fashioned cocktail garnished with bourbon soaked cherries.

Garnish with a cherry or 2 and serve immediately.

When to Serve a Chocolate Old Fashioned

  • The chocolate & cherry notes make it a perfect Valentine’s Day Cocktail. If you have a couple with very different tastes, try making his and hers cocktails. Make a Love Potion Cocktail as the second option!
  • Serve a cherry old fashioned as an after-dinner drink.
  • Make one in the fall and sip it around a cozy fire.
A cherry and chocolate old fashioned cocktail.

More Whiskey Drinks

Holding a chocolate and cherry old fashioned.

What’s your favorite way to enjoy an Old Fashioned? Let me know in the comments!


Cherry and Chocolate Old Fashioned Cocktail

A cherry and chocolate old fashioned cocktail.

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5 from 1 review

A twist on a traditional old fashioned cocktail with black cherry whiskey, chocolate bitters, cherries, and a sugar cube. Served on the rocks.

  • Author: Mandi
  • Prep Time: 5 minutes
  • Cook Time: 0 minutes
  • Total Time: 5 minutes
  • Yield: 1 cocktail 1x
  • Category: Cocktail
  • Method: Muddle
  • Cuisine: American


Units Scale
  • 1 sugar cube
  • 1 cocktail cherry
  • 3 dashes of chocolate bitters
  • ice
  • 3 ounces of black cherry whiskey
  • 1 freshly cut piece of orange peel
  • more maraschino cherries to garnish


  1. Muddle the sugar cube, cherry, and chocolate bitters in the bottom of a rocks glass.
  2. Add the ice, whiskey, and orange peel. Then, stir briefly. 
  3. Garnish with a cherry.


  • Serving Size: 1 old fashioned
  • Calories: 243
  • Sugar: 6.2 g
  • Sodium: 0.4 mg
  • Fat: 0 g
  • Carbohydrates: 7.9 g
  • Fiber: 0.8 g
  • Protein: 0.1 g
  • Cholesterol: 0 mg

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One Comment

  1. We made this with Jim Beam cherry and it was delicious. My husband loves a good old fashioned and he loved this version. We’ll have to try out Junction 35 sometime!

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