Chocolate Whoopie Pies with Raspberry Buttercream

A traditional whoopie pie is a pair of cake-like chocolate cookies sandwiching a fluffy, marshmallow frosting center. It’s a good combination, to be sure, but whoopie pies are a lot more interesting when you mix things up with different flavors and, fortunately, it is very easy to add some flavor to a whoopie pie. These Chocolate Whoopie Pies with Raspberry Buttercream pair soft, chocolate cake and a fruity raspberry filling. Flavor-wise, it’s a great combination, but the bright colors in the finished dessert make this a lot of fun, too.

The cake portion of the whoopie pies is a simple, chocolate cake that has a generous amount of cocoa powder in it to ensure that each pie has a strong chocolate flavor. They’re moist and tender, but they are a little sturdier than chocolate cupcake would be so that they are easy to handle when filling and serving. The raspberry filling is a simple American buttercream – butter, vanilla and confectioners’ sugar – spiked with some raspberry puree. You can buy the puree at some stores, but I make batches by defrosting frozen berries and pureeing them in the food processor, then straining out the seeds. It takes a little extra time to make a puree, but they pack a lot of flavor and the raspberry really turned this buttercream a beautiful shade of pink. Chocolate and raspberry is a good flavor combination in any kind of dessert and this one is no exception.

The recipe makes about 16 generously sized whoopie pies, so they’re good for serving to a crowd or at a party. I think they’re an especially good Valentine’s Day treat because of the lovely pink filling inside of the pies. They keep well for several days when stored in an airtight container and they can even be frozen if you want to tuck one or two away for another day.

Chocolate Whoopie Pies with Raspberry Buttercream
1 3/4 cups all purpose flour
1 tsp baking soda
1/2 tsp salt
1/2 cup butter, room temperature
1 cup sugar
1 large egg
1/2 cup unsweetened cocoa powder
1 tsp vanilla extract
1 cup milk

Preheat oven to 375F. Line a baking sheet with parchment paper.
In a medium bowl, whisk together flour, baking soda and salt.
In a large bowl, cream together butter and and sugar until light. Beat in egg, followed by cocoa powder and vanilla extract. Mix until everything is well combined.
Stir in half of the flour mixture, followed by the milk. Stir in the remaining flour mixture, mixing until no streaks of dry ingredients remain and batter is uniform.
Drop dough into 2 tbsp sized balls onto prepared baking sheet, leaving about 2 inches between each ball to allow for spread.
Bake for 11-13 minutes, until cakes spring back when lightly pressed.
Cool on the baking sheet for 2-3 minutes, then transfer to a wire rack to cool completely.
When cooled, pair off the whoopie pies by size and fill each pair of cookies with Raspberry Buttercream (recipe below).

Makes about 16 whoopie pies.

Raspberry Buttercream
1 cup butter, room temperature
1/4 cup raspberry puree, strained
1 tbsp milk
1 tsp vanilla extract
approx 3 cups confectioners’ sugar

In a medium bowl, beat butter until very soft. Add raspberry puree, milk, vanilla and about 2 cups of confectioners’ sugar. Beat until very smooth, adding remaining confectioners’ sugar as needed to thicken the frosting to a fluffy and spreadable consistency.