Kentucky Derby Pie Cupcakes: Place Your Bets on Chocolate, Walnuts, and Bourbon

In 2004, I went to the Kentucky Derby for my birthday. There were no Kentucky Derby cupcakes there, just a lot of rain. It rained so hard that they had to shut down the betting systems due to flooding. Jonathan and I had to walk in puddles of floating cigarette butts, beer bottles, and other things I choose not to think about.

We were in the infield. For those not in the know, the infield is not the dressed up fancy hat Derby that you see on TV. In fact, you can’t really see the races from the infield except on a big screen. However, it’s a big party atmosphere and being there was a blast, especially since I won my bet!

This year’s Derby is on Saturday! My Kentucky Derby Pie cupcakes dreamed that they were in the Derby:

It was a photo finish!

What is Derby Pie?

As described on Wikipedia, “The pie is a chocolate and walnut tart in a pie shell usually with a pastry dough crust. It is also commonly made with pecans, chocolate chips and Kentucky Bourbon. Popular additions are butterscotch, caramel, and other types of nuts.”

What is a Derby Pie Cupcake?

My Derby Pie cupcakes are chocolate cupcakes with Derby Pie filling mixed in. They are topped with a bourbon buttercream mixed with more Derby Pie filling.

The Derby Pie Cupcake Recipe: The Chocolate Cake

For the chocolate cake, I used chockylit’s recipe that I featured in my Better than Sex Chocolate Cupcakes.

Makes 16 regular cupcakes.

• 1/2 C (1 stick) butter, room temperature
• 1 1/4 C sugar
• 2 large eggs, room temperature
• 3/4 C flour
• 1/2 t baking powder
• 1/4 t baking soda
• 1/4 t salt
• 1/2 C unsweetened cocoa powder
• 1/2 C milk
• 1 t vanilla

1. Beat butter until softened.
2. Add sugar and beat until light and fluffy, about 3 minutes.
3. Add eggs, one at a time, beating until well combined.
4. Measure the flour, baking powder, baking soda, salt, and cocoa powder into a small bowl and whisk to combine.
5. In another small bowl, measure out the milk and vanilla and stir to combine.
6. Add about a third of the dry ingredients to the butter/sugar and beat to combine.
7. Add about a half of the milk/vanilla and beat to combine.
8. Continue adding, alternating between dry and wet and finishing with the dry.

The Derby Pie Cupcake Recipe: The Derby Pie Filling

The second part of the Derby Pie cupcake recipe is a Derby Pie filling recipe that I got from Allrecipes. I made it with walnuts instead of pecans. However, either nut would be good.

• 1 C white sugar
• 1 C light corn syrup
• 1/2 C butter
• 4 eggs, beaten
• 1/4 C bourbon (I used a cheap – $6.95 – store brand bottle of Kentucky Bourbon. A higher quality bourbon might have been better, but I can’t report back on that.)
• 1 t vanilla extract
• 1/4 t salt
• 1 C semisweet chocolate chips
• 1 C chopped pecans

1. In a small saucepan, combine sugar, corn syrup, and butter.
2. Cook over medium heat, stirring constantly, until the butter melts and the sugar dissolves.
3. Cool slightly.
4. In a large bowl, combine eggs, bourbon, vanilla, and salt. Mix well.
5. Slowly pour the sugar mixture into the egg mixture, whisking constantly.
6. Stir in chocolate chips and pecans.

Kentucky Derby Pie Baking Instructions

1. Set aside half of the pie filling.
2. Fold 3/4 of one of the halves into the chocolate cupcake batter. You don’t need to mix it well, just give it a nice stir.
3. Fill 24 cupcake liners about half way.
4. Use up the remaining 1/4 of the first half by putting an additional spoonful or two of the pie filling on top of each cupcake being careful not to fill them more than 3/4.
5. Line a baking sheet with parchment paper and pour the second half of the pie filling onto the baking sheet. This is going to be used in the frosting.
6. Bake both the cupcakes and the filling on the baking sheet for 20-25 minutes at 350 degrees. I baked mine at the same time on different shelves.

Bourbon Buttercream Frosting with Kentucky Derby Pie Filling

• 1 C (2 sticks) butter, room temperature
• 4 C powdered sugar
• 3 T bourbon
• 1 t vanilla
• Baked and cooled pie filling (see above for directions)

1. Cream butter and sugar.
2. Add bourbon and vanilla.
3. Stir in baked and cooled pie filling.

Because of the nuts, this is a spreadable frosting rather than a piped one. It won’t look as pretty as some other frostings, however it is still sure to be a winner at your Kentucky Derby party!