Peppermint Brownie Whoopie Pies

The holiday season, when it comes to food, is all about specific flavors. Eating combinations of these flavors – orange and clove, vanilla and nutmeg, cranberry and pistachio, etc. – will make you think of the holidays no matter what form they turn up in. I also feel this way about the combination of peppermint and chocolate, since a peppermint-kissed hot chocolate is one of my favorite holiday treats! These Peppermint Brownie Whoopie Pies are just like that mug of hot chocolate, just in a much more portable form. The bite sized cookies pack a big burst of both rich chocolate and bright peppermint flavor into every bite.

The cookies I used for these whoopie pies are little brownie rounds, made with a batter that uses both dark and milk chocolate. They are rich and very tender, with a great chocolate flavor. The batter is relatively thin and I always pipe it onto my making baking sheets using a piping bag (or a ziploc bag with the corner snipped off) because it is much faster and neater than trying to drop small spoonfuls of batter into place. It is also much easier to control the size of your cookies to ensure that they all turn out to be bite sized!

The brownies need to be baked and cooled before they can be filled. The filling is a peppermint and vanilla cream cheese frosting, which has a very creamy consistency that melds well with the cookies. You’ll detect a very slight tang from the cream cheese in the filling, but the dominant flavors are mint and vanilla. You can add even more peppermint extract if you want to make these extra minty, but peppermint extract is very strong and I find it is always better to be a bit conservative when adding it in to a batter or frosting. Once they are filled, the whoopie pies are rolled in crushed peppermint candies to give them a festive finished look. The peppermint candies (or candy canes) also add a bit of texture to the cookies.

Since the brownies are so moist, these whoopie pies keep very well as long as they are stored in an airtight container, so you can make them a day or two before you intend to serve them. The recipe also makes a fairly large batch, which makes these a great choice if you’re looking for a dessert for a holiday party!

Peppermint Brownie Whoopie Pies
Cookies
3 ounces dark or bittersweet chocolate chips
3 ounces milk chocolate chips
1/2 cup butter
1 cup sugar
3 large eggs
1 tsp vanilla extract
1 cup all purpose flour
1/4 cup Ghirardelli Unsweetened Cocoa Powder
1/2 tsp baking powder
1/2 tsp salt

Filling and Topping
1/2 cup butter, room temperature
3 ounces cream cheese, room temperature
3 cups powdered sugar
1 tbsp milk
1/2 tsp peppermint extract
1/2 tsp vanilla extract
1/4 cup crushed peppermint candies or candy canes

Preheat oven to 350F. Line a baking sheet with parchment paper (or prepare a mini whoopie pie pan).
In a microwave-safe bowl, melt together the bittersweet chocolate chips, milk chocolate chips and butter. Stir until smooth and allow to cool.
In a large bowl, beat together sugar, eggs and vanilla until well-combined. Stir in cooled, melted chocolate mixture.
In a medium bowl, sift together flour, cocoa powder, baking powder and salt. Whisk into the chocolate mixture, mixing just until everything comes together and no streaks of dry ingredients remain.
Pour batter into a piping bag (or a large ziploc bag with the corner snipped off) and pipe quarter-sized dollops of batter onto a parchment-lined baking sheet. Cookies will spread slightly as they bake, so leave about an inch between rounds of batter.
Bake for 5-7 minutes, until the cookies are set. Slightly larger cookies may need an additional minute or two of baking time.
Allow to cool completely on the baking sheet.

Make the filling: In a large bowl, beat butter and cream cheese together until smooth. Blend in milk, peppermint extract and vanilla extract. Gradually beat in the confectioners’ sugar until icing is thick and fluffy.

Assembling and Decorating: Generously spread filling between cooled cookies and sandwich them together. Roll exposed edges in crushed peppermint candies.

Makes about 36-40 mini whoopie pies.