Cooking time: 25 min
Difficulty: Difficult - for experienced cooks
Ingredients for cherry pies:
â€¢ 2, 16-oz batches pie crust dough (your favorite recipe or store-bought, enough to make 2 two-crust pies)
â€¢ 1 cup cherry pie filling
Ingredients for cupcakes:
â€¢ 4 ounces unsweetened chocolate, broken or chopped into small pieces
â€¢ 1½ cups plus 2 tablespoons whole milk
â€¢ ¾ cup (1½ sticks) unsalted butter, at room temperature
â€¢ 1½ cups granulated sugar
â€¢ 3 large eggs
â€¢ 2 teaspoons vanilla extract
â€¢ 2 teaspoons baking powder
â€¢ ½ teaspoon baking soda
â€¢ ¼ teaspoon salt
â€¢ ½ cup unsweetened cocoa powder
â€¢ 2½ cups unbleached all-purpose flour
Ingredients for frosting:
â€¢ 1 cup (2 sticks) unsalted butter, at room temperature
â€¢ 2 cups powdered sugar
â€¢ Seeds from ½ vanilla bean
â€¢ 2 tablespoons whole milk, if needed
â€¢ 24 maraschino cherries, for garnish
1. To make the mini cherry pies, preheat the oven to 375°F and grease a 24-cup miniature muffin tin. Use a rolling pin, roll out the pie crust dough on a lightly floured smooth surface until the dough is about 1/4 inch thick. Then use a 2½-inch circular cookie cutter to cut out 48 small circles.
2. Press the dough circles into the prepared tin and fill them three-quarters full of cherry pie filling.
3. Top each pie with another dough circle, sealing the pies by pinching the edges of the bottom crust to the top crust. Use a sharp knife to cut a small X into the top of each pie. Bake the pies for 10 to 12 minutes, until the edges of the crust have browned. They may overflow a bit, and thatâ€™s okay. They donâ€™t have to look perfect since theyâ€™re going into a cupcake! Allow the pies to cool for 10 minutes in the pan and then carefully transfer them to a wire rack to finish cooling while you mix the cupcake batter.
4. To make the cupcakes, turn the oven temperature down to 350°F. Line 2 standard muffin tins with 24 paper liners. Place the chocolate and 2 tablespoons of the milk in a small microwave-safe bowl and microwave for 20 seconds on high. Stir and microwave for another 20 seconds. Stir the mixture until the chocolate has melted completely and the cream is fully incorporated. Place the bowl in the refrigerator so it can cool while you prepare the rest of the cupcake batter. Use a stand mixer fitted with the paddle attachment or a hand mixer on medium speed to combine the butter and sugar for 90 seconds, until fluffy. Add the eggs, one at a time, mixing in each egg completely before adding the next. Use a spatula to scrape down the sides of the bowl. Then, with the mixer on medium-low speed, add the vanilla, baking powder, baking soda, and salt. Add the cocoa powder. Turn the mixer up to medium-high speed and mix for another 30 seconds, until all the ingredients are well combined. Scrape down the sides of the bowl and then add the flour, ½ cup at a time, alternately with the milk, 1/4 cup at a time, mixing until each addition is completely incorporated before adding the next. Finally, with the mixer on medium-high, drizzle in the cooled chocolate mixture. Continue to mix the batter on medium-high speed for 30 seconds, until smooth and creamy.
5. Spoon a heaping tablespoon of batter into the prepared tins. Place a cooled cherry pie into the center of the batter and press it gently toward the bottom. Cover the pie with another heaping tablespoon of batter so the top and sides are completely covered and the cup is about three-quarters full. Bake for about 25 minutes, until the edges and tops of the cupcakes have set and the cake springs back when you gently press your finger into the top of it. Allow the cupcakes to cool in the tin for at least 10 minutes before moving to a wire rack to cool completely.
6. For the frosting, whip the butter for about 30 seconds with a stand mixer fitted with the whisk attachment or a hand mixer on medium speed. Add the powdered sugar, ½ cup at a time, whipping on medium-high speed until fluffy. Add the vanilla seeds and whip until just combined. If the frosting is too thick, add the milk and whip on high for 20 seconds. Pipe or spread the frosting on top of the cooled cupcakes. Top each cupcake with a cherry.