Chocolate-Chocolate Whoopie Pies

What’s better than a classic whoopie pie made from tender chocolate cake and pillowy cream filling? What about a doubled down chocolate on chocolate sandwich made with decadent cakes and a tangy chocolate cream cheese frosting? We thought you might like that. If you have a cookie or truffle scoop, use it to divide up the batter into even mounds. Just keep a glass of hot water next to your work station and dip the scoop in it from time to time. A quick rinse will keep your scoops tidy. Use a resealable plastic bag to make piping on the filling extra easy.

chocolate-whoopie-pies
Photo by Alison Miksch
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  • Makes 18 (serving size: 1 whoopie pie)
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What’s better than a classic whoopie pie made from tender chocolate cake and pillowy cream filling? What about a doubled down chocolate on chocolate sandwich made with decadent cakes and a tangy chocolate cream cheese frosting? We thought you might like that. If you have a cookie or truffle scoop, use it to divide up the batter into even mounds. Just keep a glass of hot water next to your work station and dip the scoop in it from time to time. A quick rinse will keep your scoops tidy. Use a resealable plastic bag to make piping on the filling extra easy.

Ingredients

  1. Check CAKES
  2. Check 4 ounces bittersweet chocolate, finely chopped
  3. Check cup hot brewed coffee
  4. Check 2 cups all-purpose flour
  5. Check ½ cup unsweetened cocoa
  6. Check 1 teaspoon baking soda 
  7. Check ¼ teaspoon table salt
  8. Check cup light brown sugar
  9. Check ½ cup (1 stick) unsalted butter, softened
  10. Check 1 large egg
  11. Check 1 teaspoon vanilla extract
  12. Check cup whole milk 
  13. Check FILLING
  14. Check 1 8-oz. pkg. cream cheese, softened
  15. Check ¼ cup (½ stick) unsalted butter, softened 
  16. Check 1 teaspoon vanilla extract 
  17. Check cups powdered sugar
  18. Check ¼ cup unsweetened cocoa
  19. Check teaspoon table salt
  20. Check 1 to 2 tablespoons whole milk

Directions

  1. Prepare the Cakes: Preheat oven to 350°F. Place chopped chocolate and coffee in a small microwaveable bowl; microwave on HIGH until chocolate melts, about 20 seconds. Stir until smooth. Cool to room temperature, about 10 minutes.
  2. Whisk together flour, cocoa, baking soda, and salt in a medium bowl.
  3. Place brown sugar and butter in a large bowl; beat with an electric mixer on medium speed until creamy, 3 to 4 minutes. Add egg and vanilla; beat until well combined, 1 to 2 minutes. Add cooled chocolate mixture; beat until incorporated. Add flour mixture and milk alternately to brown sugar mixture, beginning and ending with flour mixture. Beat on low speed just until incorporated after each addition.
  4. Using a medium (about 1½-inch) cookie scoop, drop 36 level spoonfuls of batter 3 inches apart on baking sheets lined with parchment paper. Bake in preheated oven until set, 8 to 9 minutes. Cool cakes on pans 5 minutes; transfer to a wire rack and cool completely, about 20 minutes.
  5. Prepare the Filling: Combine cream cheese and butter in a large bowl. Beat with an electric mixer on medium speed until smooth; beat in vanilla. Sift together powdered sugar, cocoa, and salt in a medium bowl. Add powdered sugar mixture and 1 tablespoon of the milk alternately to cream cheese mixture, beating on low speed just until blended after each addition. Beat in up to 1 tablespoon more milk, 1 teaspoon at a time, until desired consistency is reached.
  6. Spread about 2 rounded tablespoons of Filling on bottom half of each of 18 cakes; top with remaining 18 cakes.