I’ve made a few kinds of whoopie pies, but I think it has been a couple of years since I’ve made them. I went out looking for an interesting flavor to try. My husband is a big fan of chocolate chip cookies, so when I found these, I thought they would be great. The original recipe paired the pies together with banana frosting, but I am not a fan of banana. What flavor of frosting should I use? We’ve had house guests this week, so I asked. Mint? Peanut butter? Caramel? Caramel: that sounded good so I searched for a recipe and found a simple one.
The dough for these is a cross between cake batter and cookie dough, which gives you the characteristic cake-like texture of the whoopie pie. I like to make any type of sandwich cookie fairly small. The original recipe said that this makes 24 sandwiches, but I made nearly three and a half dozen. These cookies might seem soft and even a little under baked, but just remember that these cookies are supposed to be cakey.
The frosting you want to be a little bit stiff, so I think that I added just over 4 cups of powdered sugar. If the frosting is too thick, add some more cream. I was hesitant to sandwich the cookies together with frosting that was warm, so I refrigerated it for a short while. This frosting does harden as it sits, so I did add a couple of drops of cream and mixed it for a couple of seconds after refrigerating. I like to pipe the frosting, as it is 100 times faster than any other way. I really liked these. The caramel is the perfect pair for the chocolate chip cookies!
Chocolate Chip Whoopie Pies with Caramel Frosting
2-1/4 cups flour
1-1/2 teaspoon baking powder
1/2 teaspoon salt
4 tablespoons butter, softened
4 tablespoons shortening
1/2 cup sugar
1/2 cup brown sugar
1/2 cup buttermilk
2 teaspoons milk
1 teaspoon baking soda
1 teaspoon white vinegar
1/2 teaspoon vanilla
1 cup mini chocolate chips
½ cup butter
1 cup brown sugar
1/3 cup heavy cream
1 teaspoon vanilla
¼ teaspoon salt
About 4 cups powdered sugar
Preheat oven to 375 degrees. Line two baking sheets with silicone baking mats.
In a small bowl, combine the flour, baking powder, and salt. Set aside. In a large mixer bowl, cream the butter and shortening. Add the sugar and brown sugar and mix to combine. Add the eggs, one at a time, beating after each addition. Stir in the buttermilk.
In a small bowl, combine the milk, baking soda, and vinegar. Add this mixture and the flour mixture to the dough and mix until combine. Add the mini chocolate chips and stir on low until incorporated.
Using a small cookie scoop (half a tablespoon), scoop the dough onto the prepared baking sheets. Bake for 9-10 minutes, or until the cookies start to brown and are set. They will be a little soft. Let the cookies cool on the cookie sheet for 5 minutes before transferring to a wire rack to cool completely.
Make the frosting: Melt the butter in a small saucepan over medium heat. Add the brown sugar and cream. Cook for 2 minutes or until sugar dissolves, stirring frequently. Remove from the heat and transfer the mixture to a large mixer bowl. Stir in the vanilla and salt. With the mixer running on low, add the powdered sugar one cup at a time, mixing until the frosting is the consistency you want.
Match the cookies in pairs of similar size. Spread or pipe the frosting on half of the cookies; sandwich with the other cookie.