Orange Chocolate Chip Cupcakes with Bourbon Buttercream Frosting (a.k.a. The Old-Fashioned)

The Old Fashioned Cupcake

Last weekend, my mom, sister and I hosted a “psuedo”-surprise birthday party for my dad. I write “psuedo” because my dad, not being a fan of surprises, knew the party was happening, but was not made privy to the guest list.  So he was certainly surprised to see over fifty of his closest friends and family show up to celebrate.  That’s right, my dad’s a pretty popular guy. 

The Old Fashioned Cupcake Ingredients

Orange Zest

My parents live in an old, 18th century townhouse in a small town in Bucks County, Pennsylvania, and what the house lacks in space it certainly makes up for in charm and character.  But scanning over a guest list of fifty people the week before the party, I was a little concerned with fitting everyone into my parents quaint home. Not only that, I was more than a little nervous about catering a party of this size.  Oh yea, did I mention that part? I was asked to help cook. My mom, sister and I would take on catering for the party, which I was really excited about. I believe I’ve mentioned that both my parents are foodies, so it would make sense that most of their friends are foodies as well.  Over e-mail, text and phone, my mom, sister and I put together an extensive heavy hors d’oeuvres menu.

Cake Batter

Old Fashioned Cupcakes

The day before, my sister and I took a tour of some of New York’s finest purveyors, picking up cheese and pâté from The Bedford Cheese Shop, dried fruit and cured meats from Eataly, and the most amazing bread from Amy’s Bread. Once we got to Pennsylvania, we picked up groceries for the rest of the menu: Swedish Meatballs, caramelized onion tarts with feta cheese, spinach artichoke dip, tapenade, smoked sturgeon dip, Puffed Pastry with sopressata and gruyere, two types of bruschetta, roasted tomatoes with ricotta and figs and mascarpone, and, perhaps my favorite item on the menu, rosemary salted nuts.  But of course the one thing I’m missing, the one thing a birthday party is certainly not complete without: cake!  And of course this could be no ordinary cake, after all this cake for the best dad in the world, my dad, Ernie.

Old Fashioned Cupcakes

Ernie has always had an affinity for good quality Bourbon. So I thought it would be appropriate to mirror his cake off of one of his favorite cocktails: The Old Fashioned. If you’re not familiar with the Old Fashioned, I recommend you order it the next time you’re out, as it’s one of the most delicious ingredient combinations I can imagine.  It’s a very simple recipe: maraschino cherries, sugar and bitters, muddled in a glass.  Add whiskey and an orange peel, stir and serve. The recipe is not much more complicated.  For his birthday, I doubled the recipe listed below and made a three-tiered rectangle cake, layered with bourbon chocolate ganache and cherry preserves, and thickly covered with the bourbon buttercream frosting. If you have an occasion to feed a large crowd, feel free to do the same, but I provided the smaller version, in cupcake form, to make it a bit more accessible.  I promise that anyone with this birthday (cup)cake will have a very happy birthday indeed.

Old Fashioned Cake

Orange Chocolate Chip Cupcakes with Bourbon Buttercream Frosting (a.k.a. The Old-Fashioned)

  • Servings: ~2 dozen cupcakes
  • Difficulty: easy
  • Print

Note: This is an adult cake recipe and the icing has a strong taste of liquor, so I wouldn’t recommend the icing for a kids party.  Feel free to substitute with a standard vanilla buttercream or cream cheese icing. If you want to add an extra splash of the brown sauce, heat 1/4 cup bourbon with a tablespoon of sugar to dissolve.  Brush the top of each cupcake with the liquor and then frost. If you’re assembling a layer cake, brush each layer with the sauce.  It makes it that much better.

Adapted from Ina Garten



  • 1 cup (2 sticks) butter at room temperature
  • 2 cups granulated sugar
  • 4 large eggs at room temperature
  • 1/4 cup grated orange zest (from 3-4 large oranges)
  • 3 cups all-purpose flour plus 2 tablespoons
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon kosher salt
  • 1/4 cup freshly squeezed orange juice
  • 3/4 cup buttermilk
  • 1 teaspoon pure vanilla extract
  • 1 tablespoon good Bourbon
  • 2 cups semisweet chocolate chunks
  • 24 maraschino or brandied cherries

Bourbon Buttercream Frosting

  • 1 cup (2 sticks) butter at room temperature
  • 5 cups confectioner sugar (sifted)
  • 1/4 cup good Bourbon
  • 1 teaspoon pure vanilla extract


For the cupcakes:

Preheat the oven to 350 degrees Fahrenheit. Line 2 cupcakes pans with cupcake liners.

In a large bowl, beat the butter and sugar together with an electric mixer on high speed until light and fluffy.  Add the eggs and the orange zest and beat until smooth.

In a medium bowl, sift together 3 cups of flour, baking powder, baking soda and salt and set aside.  In a separate bowl, whisk together the orange juice, buttermilk, vanilla ad bourbon.

Add a third of the flour mixture to the creamed butter and beat until combine.  Then add a third of the buttermilk mixture and mix until incorporated.  Repeat twice, alternating the flour and buttermilk until the batter is evenly mixed.  Toss the chocolate chips with the remaining 2 tablespoons of flour (this will coat the chocolate to ensure they don’t sink to the bottom) and fold in the chips.

Fill the cupcake foils to about 2/3rds full with batter, and bake in the oven for 20-25 minutes, until cake rises and is lightly golden browned.

For the icing:

In a large bowl, beat the butter and the confectioner sugar together until light and fluffy – about 5 minutes.  Add the bourbon and vanilla and beat until icing is thick and smooth.  If the icing seems too thick, add in more bourbon, a tablespoon at a time until it is the right consistency.  If it is too thin, add in more confectioner sugar, 1/4 cup at a time until it is the right consistency.  Transfer the icing to a piping bag fitted with a star tip, and ice the cupcakes. Top each cupcake with a maraschino cherry.

Cupcakes will keep for 3 days at room temperature, kept in an air-tight container.


5 thoughts on “Orange Chocolate Chip Cupcakes with Bourbon Buttercream Frosting (a.k.a. The Old-Fashioned)

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