Chocolate Chip Whoopie Pies with Chocolate Chip Buttercream Filling

Whoopie pies may look like sandwich cookies, but their cake-like texture puts them closer to a cupcake than to your average cookie. That doesn’t mean that whoopie pies can’t come in some classic cookie flavors, however, and these Chocolate Chip Whoopie Pies with Chocolate Chip Buttercream Filling are proof of that. They taste like a chocolate chip cookie – with plenty of butter and vanilla flavor, a hint of salt and lots of chocolate chips – but have a cupcake-like texture and lots of creamy filling.

The whoopie pies start out with a simple buttermilk cake batter. A relatively small amount of batter gives you plenty for the whole batch of pies. The batter has a hint of brown sugar flavor to it, but is not too sweet, so it balances the sweet and creamy filling very well. In fact, they’re better with the filling than without- but that is the way a whoopie pie should be. Adding a pinch of salt to the filling really helps capture the flavor of a chocolate chip cookie in every pie.

I make these pies a little smaller than your average whoopie pie, and get about 16 pies from this batch, which means that you need to make 32 individual cookies. I like the look and flavor of full sized chocolate chips, even though the pies are a little on the smaller side, but if you have mini chocolate chips you can substitute them in to both the whoopie pie batter and the filling. Dark and semisweet chocolate chips are good choices, blending them with some white chocolate chips makes a lovely variation if you like your pies a little bit sweeter.

Chocolate Chip Whoopie Pies with Chocolate Chip Buttercream Filling
1 1/4 cups all purpose flour
1/2 tsp baking soda
1/4 tsp salt
1/4 cup butter, room temperature
1/4 cup brown sugar
1 large egg
1 tsp vanilla extract
1/2 cup buttermilk
2/3 cup chocolate chips

Preheat oven to 350F. 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 brown sugar until light and fluffy. Beat in egg and vanilla until well combined.
Stir in half of the flour mixture, followed by the buttermilk. Stir in remaining flour, mixing just until no streaks of dry ingredients remain. Stir in chocolate chips.
Drop tablespoonfuls of batter, making them as round as possible, onto prepared baking sheet. You will need 32 individual cookies.
Bake for 11-14 minutes, until cookies are set and spring back when lightly pressed.
Cool on a wire rack completely before filling.

Filling
1/3 cup butter, room temperature
1 tbsp milk
1 tsp vanilla extract
pinch salt
1-1 1/2 cups confectioners’ sugar
1/2 cup chocolate chips, coarsely chopped (or mini chips)

In a medium bowl, beat together butter, milk, vanilla and salt until well combined. Gradually beat in the confectioners’ sugar until filling is smooth and creamy. It should not be quite as stiff as a regular buttercream frosting. Stir in chocolate chips.
Spread in between cooled whoopie pies.