Chocolate Orange Old Fashioned Recipe

by Tonya Staab

With homemade orange simple syrup, chocolate bitters, and Jefferson’s Ocean Bourbon this Chocolate Orange Old Fashioned will be a favorite.

chocolate orange old fashioned
This chocolate orange old fashioned drink served with a truffle will become your favorite cocktail.

I’ve partnered with Jefferson’s Bourbon to create this cocktail. Make sure to get your tickets to Bourbon + Beyond this year.

Two of my favorite flavors (next to bourbon, of course) are chocolate and orange. One of my favorite candies, when I was younger, was Jaffas, and if you haven’t tried a chocolate-orange Aero bar you are missing out. I recently came across a box of dark chocolate orange truffles and they inspired me to create this cocktail.

Chocolate orange old fashioned

Before you start making our chocolate orange old fashioned, you need to do two things.

  1. Freeze large ice cubes
  2. Make our orange simple syrup recipe

Orange simple syrup

homemade orange simple syrup in a glass bottle
Make our homemade orange simple syrup recipe to use in your chocolate old fashioned.


  • 2 cups water
  • 2 cups sugar
  • Juice from half an orange
  • Zest from one orange


Add the orange juice, water, sugar, and orange zest to a small saucepan. Cook on medium-high heat, stirring occasionally. As you bring it to a boil the sugar will dissolve.

Remove from the heat and then strain your orange simple syrup to remove the zest pieces. Allow it to cool to room temperature and then pour it into a bottle or canning jar.

Store in the refrigerator for up to two weeks.

Chocolate orange old fashioned recipe

chocolate orange old fashioned

Chocolate Orange Old Fashioned

Serves: 1 Prep Time: Cooking Time:
Nutrition facts: 200 calories 20 grams fat
Rating: 4.7/5
( 3 voted )


  • 1 large ice cube
  • 1 oz Jefferson’s Ocean Aged at Sea® Bourbon
  • 1/4 oz orange simple syrup
  • 3 dashes chocolate bitters
  • Garnish with orange peel and a chocolate orange truffle


  1. Place the ice cube in the glass.
  2. Add the bourbon, orange simple syrup, and chocolate bitters.
  3. Stir your old fashioned.
  4. Use a food pick to cradle a chocolate orange truffle in a slice of orange peel to garnish your cocktail.
orange simple syrup being added to an old fashioned drink
Add orange simple syrup and chocolate bitters to your chocolate orange old fashioned.

Jefferson’s Bourbon – the bourbon known for pushing the boundaries – is a primary sponsor of Bourbon + Beyond this year! If you haven’t been to Bourbon + Beyond, the over-the-top festival filled with music, food, and of course, BOURBON, it’s a must-do for every bourbon lover.

jefferson's bourbon old fashioned
Jefferson’s Ocean Aged at Sea® Bourbon with chocolate bitters and homemade orange simple syrup makes a delicious old fashioned.

More bourbon cocktails

Are you looking for even more bourbon cocktails? Take a look at these ones; you can even use Jefferson’s Bourbon in some.

Please pin this post for later:

chocolate orange old fashioned pinterest

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