Peppermint Chocolate Whoopie Pies

My chocolate whoopie pies got a xmas make-over, peeps, and suffice is to say my ten-year old taste tester went kind of berserk. And I mean that in the best way. Chocolate and peppermint are his favorite flavor combo, candy canes one of his favorite candies, these particular peppermint Newman O’s, his favorite store-bought cookie, and the peppermint chocolate icebox cake from the book Icebox Cakes, his favorite cake. (Full disclosure: his mom wrote said book and he’s likely a tad biased).I first made these for an adults-only pre-xmas xmas party and said taste-tester was not happy. At my husband’s insistence, I generously, okay reluctantly, shared one with him on my way out the door, and promised I’d be making them again some time soon. I had tons of leftover mint buttercream filling and so keeping my promise proved to be easy. I made them again exclusively for the taste-tester and his brother, and then again for the kids who trashed our basement/attended our New Year’s Eve party.

And each time I have made them, be it for adults or kids or basement-trashers, the pies have been consumed with much enthusiasm. We always made peppermint chocolate whoopie pies around the holidays at baked, and I don’t know why it has taken me this long to incorporate the treat into my own holiday baking regime. But i’m on board now and here’s why you should be too: 

The cookies are fast and easy to make. The buttercream is a breeze, and people (at least the people I hang with) go berserk for them. Moreover, you can freeze the pre-filled cookies and refrigerate the buttercream kind of indefinitely (sorry food-safety police, but I think i’m right), ensuring you have whoopie pies at a moment’s notice (provided you bring your buttercream to room-temp prior to assembly). AND — even better — you can assemble and decorate these suckers and then freeze them, so that they are ready to pull out and serve LITERALLY whenever you so desire. I love a do-ahead dessert — always have and always will. And I love a whoopie pie almost more. In short, there’s a lot of love surrounding these pies and I suggest that you get right in there with me, and enjoy some of it.

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Peppermint Chocolate Whoopie Pies

Recipe Author Jessie Sheehan

Course Dessert

Ingredients

• For the pies
• 1 3/4 cups all-purpose flour
• 1 teaspoon baking powder
• 1/2 teaspoon baking soda
• A rounded 1/4 teaspoon kosher salt
• 1/2 cup shortening
• 2 tablespoons unsalted butter room temperature
• 1 1/4 cups packed dark brown sugar
• 2 egg yolks
• 1 tablespoon pure vanilla extract
• 3/4 cup Dutch processed cocoa powder
• 1 teaspoon espresso powder
• 1/2 cup boiling water
• 3/4 cup buttermilk room temperature
• For the peppermint filling
• 1 1/2 cups unsalted butter room temperature
• 6 cups confectioners' sugar sifted if lumpy
• 1/2 to 3/4 cup of heavy cream room temperature
• 1 to 2 teaspoons peppermint extract
• 1/2 teaspoon kosher salt
• 3 to 5 crushed candy canes for decorating

Instructions

• Preheat the oven to 350 degrees.
• In a medium bowl, whisk the flour, baking powder, baking soda and salt.
• 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 saran wrap, for 30 minutes.
• Line two baking sheets with parchment paper and drop 1 1/2 tablespoons of batter 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. Repeat with the remaining batter. 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 a cup at a time, keeping the mixer at the same low speed and alternating with the cream.
• 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 the all of the sugar and cream has been incorporated. Add the extract and salt and mix again. Continue mixing on medium-low 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.
• Place the crushed candy canes in a shallow bowl (you can crush them in a plastic 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 plastic wrap, for up to three weeks. Bring to room temp before serving.

Notes

The buttercream recipe makes A LOT — I ended up making several batches of pies in order to use it all up. Feel free to halve the recipe.