Grasshopper Whoopie Pies by Jessie Sheehan

Grasshopper Whoopie Pies, for the uninitiated, are deeply chocolate-y cake-like cookies, filled with a minty, green buttercream. They are the loveliest of spring-time treats, and I have a 13 year-old, with an April birthday, who asks for them every year when we celebrate him. The cookies are easy to make and bake up in minutes, and the frosting, too, comes together speedily. I like to roll the edges of mine in green sparkling sugar, to zhuzh them up a bit. If you love the combo of mint and chocolate, but are not feeling the green color of these, I also like to tint these pink (my favorite color, FYI). But leaving the filling white is also an option. Any way you color these (or don’t) they are a truly festive and much appreciated spring-y sweet in which I highly recommend you indulge.

To take a peek at the original blog post for Grasshopper Whoopie Pies, and to peruse my collection of original recipes, click here.



For the pies:

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

For the grasshopper filling:

  • 1 1/2 cups, 3 sticks, unsalted butter, room temperature
  • 6 cups confectioners’ sugar, sifted
  • 1/2 to 3/4 cup 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)
  • A scant 1/2 tsp salt
  • A few drops of green food coloring
  • Green sparkling sugar for decorating

To make the pies, 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.

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 grasshopper buttercream. I used the same 1 1/2 tablespoon cookie scoop to fill the pies, as I did to scoop the cookies.

To make the grasshopper 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, 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. Add the food coloring, just a few drops, or to your liking, and mix until just incorporated.

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 green sparkling sugar in a shallow bowl. Roll the edges of the just-filled pies in the sugar.

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

FYI: the buttercream recipe makes ALOT – halve the recipe if you do not want extra . . .

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