Peppermint Chocolate Whoopie Pies

I am a whoopie pie lover from way back. For the uninitiated, a whoopie pie is a tiny sandwich made of two round, sturdy pieces of cake and filled with some kind of frosting. Here, the cakes are chocolate, and the filling, a peppermint buttercream. To finish, the edges of the cream are rolled in crushed candy canes because: Christmas. Back in the day when I slogged away in a bakery, if an opportunity ever presented itself to sneak a treat, I always went for the whoopie pies. And on birthdays, when the head baker would give you a slice of whatever cake your heart desired, I always forewent the cake for the whoopie. The assembly here is easy peasy – cakes come together effortlessly, as does the buttercream; and yet the bang for your buck is enormous. Clearly, I am not the only whoopie pie fanatic around, for when I make these for friends and family, folks go kind of bonkers (in a good way). Here’s to hoping you will, too.

To take a peek at the original blog post for my peppermint chocolate whoopie pies, and to peruse my collection of original recipes, click here.






  • 1 3/4 cup all purpose flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • rounded 1/4 tsp salt
  • 1/2 cup shortening
  • 2 Tbsp unsalted butter, room temperature
  • 1 1/4 cup packed dark brown sugar
  • 2 egg yolks
  • 1 Tbsp pure vanilla extract
  • 3/4 cup dutch processed cocoa powder
  • 1 tsp espresso powder
  • 1/2 cup boiling water
  • 3/4 cup buttermilk, room temperature


  • 3 sticks of unsalted butter, room temperature
  • 6 cups of confectioners’ sugar, sifted
  • 1/2 to 3/4 cup of heavy cream, room temperature
  • 1 1/2 to 3 tsps peppermint extract, or to taste (i made mine with 4 tsp and it was very minty)
  • scant 1/2 tsp salt
  • 3 to 5 crushed candy canes for decorating


preheat the oven to 350 degrees.

in a medium-sized bowl, whisk the flour, baking powder, baking soda and salt together and set aside.

in the bowl of a stand mixer, fitted with the paddle attachment, combine the shortening, butter, and sugar, and mix on medium-low speed until slightly fluffy, scraping down the bowl with a rubber spatula, as needed. add the yolks and vanilla and mix again on medium low until just incorporated.

meanwhile, place the cocoa and espresso powders in a small bowl and add the boiling water. whisk until combined and add this chocolate mixture to the stand mixer bowl and mix on medium low to combine, scraping down the bowl with a rubber spatula as needed.

add the dry mixture in three additions to the stand mixer bowl, alternating with the buttermilk in two additions, and ending with the dry. take the bowl off the mixer when there is still unincorporated flour in the dough and finish mixing by hand with a rubber spatula. let the dough rest on the counter, lightly covered with plastic wrap, for at least 30 minutes (we always did this at the bakery, as it helps the whoopies keep their shape when baking).

line two baking sheets with parchment paper and drop 1 1/2 tablespoons of dough about 1-inch apart on the sheets. bake for 8 to 10 minutes, rotating the pans halfway through the baking time until the cookies are dry to the touch and bounce back when lightly pressed. let cool completely before filling with the below peppermint buttercream. i used the same 1 1/2 tablespoon cookie scoop to fill the pies, as i did to scoop the cookies.


place the butter in the bowl of a stand mixer fitted with the paddle attachment and beat on low to medium-low until smooth. about 3 minutes. begin adding the sugar, only a half cup at a time, keeping the mixer at the same low-ish speed. once about a third of the sugar is incorporated, stop the mixer and scrape the bowl with a rubber spatula. return the mixer to the same speed, and add about 1/4 of the cream, mixing until incorporated.

continue slowly mixing in this fashion (adding sugar and cream, scraping with a spatula periodically, and taking time to let the mixer run in between additions), until most of the sugar and cream has been incorporated. add the peppermint and salt, mix again and add the remaining sugar and cream. continue mixing on medium-low (at the highest) for at least 5 to 10 minutes, if not longer. the frosting will be quite light, creamy, and fluffy when it is done. store the frosting tightly covered at room temperature for up to 24 hours or refrigerate it for up to one month. bring the frosting to room temperature prior to using. and you may need to rewhip it in your mixer.

place the crushed candy canes in a shallow bowl (you can crush them in a zip lock bag with a rolling pin or in a food processor. roll the edges of the just filled pies in the candy.

serve whoopies immediately, or freeze on a cookie sheet, covered with saran wrap, for up to three weeks. bring to room temp before serving.


the buttercream recipe makes ALOT – i ended up making several batches of pies in order to use it all up. feel free to halve the recipe.

as noted in my post, i froze the pies filled and decorated with great results. i placed them on a tray and in the freezer, and once they were frozen solid, i covered them in plastic wrap. i brought them to room temp before serving. i’ve also frozen the cookies unfilled on a sheet pan, and once frozen, transferred them to a zip lock bag. and i’ve kept the mint frosting in the fridge for about a month . . .


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