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Peppermint Whoopie Pies

With simple set-up, fun participatory steps along the way, and crowd-pleasing appeal, these morsels deserve a prominent place in your baking rotation.

pep whoopie pies
Jessie Sheehan Peppermint whoopie pies can be the thinking person's alternative to holiday or birthday cupcakes.

Ingredients:

For the pies:
  • 1 ¾ cups all-purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ¼ tablespoon salt (rounded)
  • ½ cup shortening
  • 2 tablespoons unsalted butter (room temperature)
  • 1 ¼ cups packed dark brown sugar
  • 2 egg yolks
  • 1 tablespoon pure vanilla extract
  • ¾ cup Dutch processed cocoa powder
  • 1 teaspoon espresso powder
  • ½ cup boiling water
  • ¾ cup buttermilk
For the peppermint filling
  • 2 sticks of unsalted butter (room temperature)
  • 4 cups confectioner's sugar (sifted)
  • 2 teaspoons peppermint extract (or more or less, to taste)
  • ¼ teaspoon salt
  • a few drops of green food coloring
  • red and green sparkling sugar (for decoration)

Steps:

  1. Step 1

    To make the pies, preheat the oven to 350˚F. In a medium-sized bowl, whisk the flour, baking powder, baking soda, and salt together and set aside.

    Sous Tip:

    Whisking is a great task for small hands—and if your brood is motivated by having tools of their own, kid-specialized whisks are out on the market. This step provides a chance to explain why bakers separate dry and wet ingredients: otherwise, the ingredients interfere with one another, harming flavor and texture consistency.

  2. Step 2

    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 until just incorporated.

  3. Step 3

    Place the cocoa and espresso powders in a small bowl and add the boiling water. Whisk until combined and add to the stand mixer bowl. Mix on medium low to combine.

  4. Step 4

    Add the dry mixture in three additions, alternating with the buttermilk in two. Stop the mixer when there is still unincorporated flour in the dough and finish mixing by hand. Let the dough rest on the counter, lightly covered with plastic wrap, for at least 30 minutes.

  5. Step 5

    Line two baking sheets with parchment paper and drop 1 ½ 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.

  6. Step 6

    To make the peppermint filling, 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, ½ cup at a time, alternating with a tablespoon or two of the cream, until all of the sugar and cream has been added. Stop the mixer and scrape the bowl with a rubber spatula, as needed.

  7. Step 7

    Add the peppermint and salt, and 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. Add a few drops of the food coloring, and mix until just incorporated.

  8. Step 8

    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.

  9. Step 9

    Place the sparkling sugars in two shallow bowls and roll the edges of half of the pies in one, and half in the other.

  10. Step 10

    Serve whoopies immediately, or freeze on a cookie sheet, covered with plastic wrap, for up to three weeks. Bring to room temperature before serving.