Rich chocolate cupcakes with a hint of orange bitters, topped with a smooth, velvety, bourbon-infused buttercream frosting and a maraschino cherry – these cupcakes are a take on the classic Manhattan cocktail and are perfect for a celebration. My partner’s favorite drink is the Manhattan, so I made these cupcakes for his birthday last month, but these are also really great for a rich post-dinner dessert, the holidays, or any kind of celebration. You can add a few more dashes of bitters to the batter if you want something to cut the richness of the cake and the frosting, but the frosting has a strong and distinct bourbon flavor already, which will be very hard to miss. I’d also suggest whipping up a Manhattan for yourself as you are baking this, so you know what sort of flavor profile to aim for.
These are best eaten the day of so that the cake does not dry out. But if you want to serve them later, I would recommend making the frosting later so that it still has the right consistency when you serve it. Or you could do what I did, which is whip an entire batch, and then use the leftovers for some much-needed energy boost, which was pretty useful as we packed furniture as part of our move from Charlottesville to New Haven (more soon on some of the lovely places that I will miss eating at in Charlottesville). For now, here’s the recipe to convert a classic cocktail into a beloved dessert.
Ingredients (makes 10-11 cupcakes)
- 1 cup all-purpose flour
- 1 cup white sugar
- 1/2 cup unsweetened cocoa
- 1 teaspoon baking soda
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
- 1 egg
- 2/3 cup cold brewed coffee
- 1/4 cup vegetable oil
- 1/2 cup + 2 tablespoons buttermilk
- 2 tsp bitters (optional)
- 1/2 cup (1 stick) butter at room temperature
- 2 cups confectioner sugar
- 2 tbsp good Bourbon
- 1 teaspoon pure vanilla extract
- Maraschino cherries
For the cupcake:
- Preheat oven to 350 degrees F (175 degrees C). Grease and flour a muffin pan or put cupcake liners into the pan.
- In a large bowl, combine the flour, sugar, cocoa, baking soda, baking powder and salt. Make a well in the center and pour in the eggs, coffee, buttermilk and oil. Mix until smooth; the batter will be thin. Pour the batter into the prepared pan.
- Bake in the preheated oven for 15-20 minutes, or until a toothpick inserted into the center of the cake comes out clean. Allow to cool.
For the topping:
- 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. Once the cupcakes are out of the oven and have cooled, ice the cupcakes (the icing will start melting if you try to top hot cupcakes). Top each cupcake with a maraschino cherry.