Bourbon Brown Sugar Cupcakes

These Bourbon Brown Sugar Cupcakes are inspired by the flavors of Derby Pie, which is often served during the Kentucky Derby. Brown sugar cupcakes have a bourbon-walnut praline center, and they’re topped with rich bourbon-spiked chocolate buttercream.

Bourbon Brown Sugar Cupcakes

The Kentucky Derby is held the first Saturday in May each year. And as a dyed-in-the-wool southerner I can’t let it pass by without celebrating it with food. I’ve said it before – I’m not really a follower of thoroughbreds, but I am a huge fan of the food that surrounds Derby Day!

This cupcake recipe starts with a brown sugar cake batter, which has a healthy dose of bourbon in the mix. A bourbon-walnut praline filling is baked right into the cupcake. Which gives it something akin to a ‘bourbon ball‘ center. Chocolate buttercream – again – spiked with bourbon, has truffle-like flavor and consistency. Toasted walnuts and mini chocolate chips give a nod to it’s inspiration – Derby Pie. Have you heard of it?

Bourbon Brown Sugar Cupcakes

Inspired by Derby Pie

To understand the inspiration for this cupcake, you first need to know about Derby Pie. It’s a famous dessert that originated in Louisville, Kentucky. Rich and decadent, it’s typically made with a filling of chocolate chips, walnuts, and bourbon. (Think pecan pie family, but with chocolate and walnuts.) While Derby Pie is not an official dish created specifically for the Kentucky Derby, it has become strongly associated with the event.

The Derby Pie recipe was created in the 1950’s by the Kern family, who own Kern’s Kitchen in Louisville. They are highly protective of their secret family recipe and the confection’s trademark name, which is why you probably won’t ever find a copycat recipe for it here.

Make the Bourbon Walnut Praline

Mix up the bourbon walnut praline filling first, since it needs to be refrigerated before use. Combine the following until well blended: toasted chopped walnuts, vanilla wafer crumbs, brown sugar, cocoa powder, corn syrup (or honey), and bourbon, of course. Put it in the refrigerator while you make the cupcakes.

Bourbon Buying Tip: Use a Kentucky bourbon that you like to drink. Or, something with a pleasing fragrance. Super fancy and expensive varieties need not apply. Just use something mid-range such as Wild Turkey 101, or a small bottle of Maker’s Mark will do the trick. 80 proof is fine. Because most of the alcohol cooks out during baking.

Make the Brown Sugar Cake Batter

Mix together dry ingredients in a large bowl: flour, baking powder, cinnamon, allspice, nutmeg, and salt. Cream together butter and brown sugar until fluffy, then add in egg one at a time. Alternate the dry ingredients with sour cream and bourbon. All of which results in a heavenly spiced fluffy cake batter.

Divide the batter between cupcake liners using a trigger ice cream scoop (such as this one). Then, with a teaspoon measure, scoop the chilled walnut praline mixture on top of each scoop of cake batter. Press the praline mixture down into the batter with the back of the teaspoon. Next, gently swirl the cake batter over the praline. Use a butter knife for this – it works well! (See video for this action.)

Bake and Cool

Bake the cupcakes in a preheated 350°F oven for about 18 minutes. When they’re done, the cupcake tops will be cracked and the filling will have bubbled up a little. Cool the cakes completely on a wire rack before frosting.

Make the Chocolate Bourbon-Spiked Buttercream

Cream together room temperature butter with confectioners’ sugar. Then add melted unsweetened chocolate (the Baker’s Bar kind) and 2 tablespoons of bourbon. If you can’t find unsweet chocolate, you can use bittersweet chocolate as a substitute. Beat everything together until thick and consistently chocolate-hued. Add in whole milk a little at a time to thin the mixture, then whip until light and fluffy.

Frost the Cupcakes

Immediately transfer the frosting to a large piping bag fitted with a French piping tip (open star, Ateco #828). Pipe one swirl of frosting onto each cupcake and immediately sprinkle on chopped walnuts and mini chocolate chips.

Note: This chocolate frosting has setting properties akin to ganache. However, not quite as firmly set. But still firm enough to clog your piping tip if you leave it at room temp for more than 30 minutes. So don’t tarry with the frosting – get to piping!

Bourbon Brown Sugar Cupcakes

Garnish your Bourbon Brown Sugar Cupcakes with black cocktail cherries. Although, this can be optional. But it’s such a nice touch. And it’s a nod to the popular Old Fashioned cocktail, made with bourbon and muddled cherries. Find them for purchase right here!

Bourbon Brown Sugar Cupcakes

And if you’re all in for the Derby theme, then you can find the cute equestrian cocktail picks I used right here.

Bourbon Brown Sugar Cupcakes

I can’t help but think these would be great for Father’s Day as well. But with their bourbon ball-like centers and lightly spiced brown sugar cake? Also fall and winter holidays. (I know, too soon!)

Bourbon Brown Sugar Cupcakes

If you’re looking for something rich, decadent, and uniquely southern – then this may be the ticket. Make them for Derby Day, Father’s Day, or for the bourbon enthusiast/aficionado in your life. Or if you’re always looking ahead (like me!) bookmark them for holiday fare. Because nothing says special occasion like a sweet treat infused with good ol’ Kentucky bourbon.

Related Recipe: Derby Pie Truffles

Bourbon Brown Sugar Cupcakes

Heather Baird
These Bourbon Brown Sugar Cupcakes are inspired by the staple dessert of the Kentucky Derby: Derby Pie. Brown sugar cake batter is infused with bourbon, and filled with a bourbon walnut-praline mixture – flavors and textures that resemble a classic bourbon ball. The bourbon-spiked chocolate buttercream makes these truly decadent, and worthy treat for watching the most exciting two minutes in sports. However, you don’t have to be a Derby fan to make these cupcakes.
See recipe notes for no-alcohol suggestions.
4.50 from 2 votes
Prep Time 20 minutes
Cook Time 18 minutes
30 minutes cooling time 30 minutes
Total Time 1 hour 8 minutes
Course Dessert
Cuisine American, Southern United States
Servings 16

Equipment

  • Decorator piping tip Ateco #828
  • Piping bag

Ingredients
 
 

Bourbon walnut praline filling

  • 1/4 cup chopped walnuts toasted
  • 1/4 cup vanilla wafer crumbs
  • 3/4 teaspoon unsweet cocoa powder
  • 1/4 cup confectioners’ sugar
  • 1 teaspoon light corn syrup or honey
  • 1 tablespoon Kentucky bourbon

Brown sugar cupcakes

  • 2 cups cake flour
  • 2 teaspoons baking powder
  • 1 1/2 teaspoons ground cinnamon
  • 1/2 teaspoon allspice
  • 1/4 teaspoon grated nutmeg
  • 1/4 teaspoon fine grain sea salt
  • 1/4 cup unsalted butter at room temperature
  • 3/4 cup light brown sugar
  • 2 large eggs
  • 3/4 cup sour cream
  • 1/4 cup Kentucky bourbon

Bourbon chocolate buttercream

  • 4 oz. unsweet chocolate chopped
  • 1/2 cup unsalted butter at room temperature
  • 2 cups confectioners’ sugar
  • 2 tablespoons Kentucky bourbon
  • 1/4 cup whole milk or cream
  • 1/4 cup chopped walnuts toasted
  • 3 tablespoons mini chocolate chips
  • 16 black cocktail cherries such as Amarena or Luxardo cherries

Instructions
 

Bourbon walnut praline filling

  • Combine the walnuts, vanilla wafer crumbs, cocoa powder, and confectioners’ sugar in a bowl. Whisk to combine.
  • Add the corn syrup and bourbon. Mix well with a rubber spatula until well blended. Refrigerate the mixture while you make the cupcakes.

Brown sugar cupcakes

  • Preheat the oven to 350°F. Line cupcake pans with 16 paper liners.
  • In a large mixing bowl, whisk together the flour, baking powder, cinnamon, allspice, nutmeg, and sea salt. Set aside.
  • In the bowl of an electric mixer, cream together the butter and brown sugar. Add the eggs in one at a time. Mix well after each addition.
  • Add 1/3 of the dry mixture to the creamed mixture and beat until just combined. Add half of the sour cream and all of the bourbon to the batter; beat until just combined. Add in another 1/3 of the dry flour mixture; mix again. Add the remaining sour cream; mix until just combined. Finally, add the last 1/3 of the flour mixture and beat until a fluffy consistent batter is achieved, about 2 minutes.
  • Portion the batter into the prepared cupcake tins (use a trigger ice cream scoop if you have one, or 1/4 cup measure). Remove the bourbon walnut praline filling from the refrigerator and scoop it by the level 1 teaspoonful. Place one teaspoon of the filling on top of each portioned cup of batter. Press the filling down into the batter using the back of the teaspoon, or with a butter knife. Gently swirl the batter over the filling (see video for this action).
  • Bake for 18-20 minutes, or until the cupcakes are well risen, the tops are slightly crackled. Let cool in the pans 5 minutes, and then remove to a wire rack to cool completely.

Bourbon chocolate buttercream

  • Place the chocolate in a microwave-safe bowl and heat in 1 minute increments at 100% power, stirring well in between heatings, until the chocolate is melted and smooth. (About 2 minutes total time.) Set aside to cool slightly.
  • Place the butter in the bowl of an electric mixer and beat on high speed until creamy. Add the confectioners’ sugar and mix on low speed at first, then medium speed, until the mixture is crumbly and partially combined. Add in the cooled melted chocolate and the bourbon. Mix again until a thick consistently chocolate frosting is achieved. Add milk and beat until light and fluffy. If mixture seems thick, add additional milk 1 tablespoon at a time until it comes to piping consistency.
  • Immediately transfer the buttercream to a piping bag fitted with a large open star tip (also called French piping tip, or Ateco #828). Pipe one swirl on top of each cupcake. Sprinkle with walnuts and mini chocolate chips. Add one cocktail cherry to each center swirl of frosting.
  • Store cupcakes air tight in a cupcake keeper, or well covered with plastic wrap.

Notes

What to expect: These cakes are rich with a sturdy brown sugar cake base filled with bourbon walnut praline. The center tastes like a classic bourbon ball. The frosting is rich and deeply chocolaty. When first assembled, you may have a slight boozy note of alcohol from the frosting, but the next day the bourbon will have mellowed and all that’s left is the nuanced flavors of the bourbon.
No Alcohol Version: It’s difficult to find a good replacement for bourbon in baking recipes. My choice is apple juice (no sugar added) mixed with a little bourbon vanilla extract. For this recipe, replace the bourbon in the filling with 1 tablespoon apple juice, and 1/4 teaspoon vanilla extract.  For the cake portion, replace the 1/4 cup bourbon with 1/4 cup apple juice with 1/2 teaspoon vanilla extract. For the buttercream, simply omit the bourbon and replace it with 1 teaspoon vanilla extract.
Pipe Swiftly: This chocolate frosting has setting properties akin to ganache. However, not quite as firmly set. But still firm enough to clog your piping tip if you leave it at room temp for more than 30 minutes. So don’t tarry with the frosting – get to piping!
What Kind of Bourbon: Use a Kentucky bourbon that you like to drink. Or, something with a fragrance that you find pleasing. Super fancy and expensive varieties need not apply. Just use something mid-range such as Wild Turkey 101, or a small bottle of Maker’s Mark will do the trick. 80 proof is fine. Because most of the alcohol cooks out during baking.
 
 
Keyword bourbon balls, bourbon chocolate buttercream, brown sugar bourbon cupcakes, brown sugar cake, Derby Day recipe, derby pie cupcakes, Kentucky bourbon, Kentucky Derby recipe, walnut praline filling
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Mary
Mary
1 month ago

4 stars
These cupcakes are beautiful and very impressive. I followed the recipe exactly (except kept the buttercream bourbon-free) but the cake itself seemed dry. After baking I realized the recipe said to use cake flour but the video says AP flour. Would that have made the difference?
Regardless, I would bake again but using all purpose flour or a different spice cupcake recipe. Thank you for all your recipes and inspiration!