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Whoopie Pies Are the New Cupcakes

Making these peppermint-powered delights is almost as much fun as saying their name.

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I did not grow up eating homemade birthday cake. Mint-chocolate chip ice cream cakes from Baskin Robbins were my jam. I loved them and, more to the point, cake-making did not interest either my mother or father. (They put their energy into lawyering, psychotherapy, and grounding me.) My children, however, celebrate each and every birthday with a homemade cake—because I make sweets and treats professionally, but also because I love cake and (for the most part) love making it.

Cupcakes? Not so much. Portioning batter into the paper liners; baking tray after tray; the frosting: I find producing cupcakes at holiday fete or school birthday party scale unbearably tedious.

Enter the whoopie pie. Whoopie pies are essentially cake sandwiches, with a fantastic filling-to-cake ratio. Often, the edge of said filling comes rolled in sprinkles or candy, so there’s that, too. When I started as a kitchen professional, they put me on whoopie pie duty early on, and I’ve loved them ever since. Meanwhile, when you want to engage kids in their own treat creation, these are easy as … well, you know. The batter comes together in a stand mixer, rests briefly on the counter, and is then scooped onto a cookie tray or two. After a lightning-fast bake, you and your assistants fill cooled pies with a good, old-fashioned American buttercream—and by “filled,” I mean you plop some frosting on the underside of one whoopie and top with another.

A final plug comes from my 13-year-old, Jack, who prefers his desserts on the less sugary side, and finds that the whoopie pie does the job on that front. For the record, I am not on the lookout for less sugary desserts, but consider this just one more sign that these are the reprieve our cupcake-saturated culture demands.

Jessie Sheehan is a cookbook author, food writer, recipe developer, and baker. She is the author of  The Vintage Baker and the co-author of  Icebox Cakes (both published by Chronicle Books). She has developed recipes for many cookbooks, besides her own, and has contributed recipes/and or written for Epicurious, Food52, Fine Cooking, TASTE, and Main Street Magazine, among others.

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.