Grasshopper Whoopie Pies for St. Paddy’s Day

Whoopie pies are, and have always been, one of my favorite sweet treats. This fact is perhaps best evidenced by the inclusion of not one, not two, but now four whoopie pie recipes—including these grasshopper whoopie pies—on this one little ole site . . . My love for them stems from my childhood addiction to Drake’s Devil Dogs (a Hostess-like packaged chocolate cake filled with whipped cream and shaped like a dog bone). Whoopie pies are the less-dry, round version of that which my after-school memories are made.Grasshopper Whoopie Pies - the perfect St. Patrick's Day dessert. | Jessie Sheehan BakesI got super into them while working at Baked,  as they make some of the best ever (in my humble opinion). And lucky for me, my kids are super into them too, particularly the younger one who is a tad hard to please when it comes to sweets. See here for more on that. Mint grasshopper whoopie pie filling | Jessie Sheehan BakesIn fact, SO into them, that they are often requested instead of birthday cake, which honestly, I am down with (full disclosure, I don’t often feel I am at my best when birthday cake making – which I know sounds kind of suspect seeing as I make sweets for a living . . . ). Anyway, that is a discussion for another day. In the meantime, the recipe here is for the spring-time, Saint Paddy Day-appropriate grasshopper whoopie pies that I make for my younger son each April on his bday. They are minty and chocolate-y and very green and the kids go bonkers when I bring these to school for bday celebrating. And I’m thinking/hoping you might, too.

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Grasshopper Whoopie Pies

Recipe Author Jessie Sheehan

Ingredients

  • For the pies:
  • 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
  • For the grasshopper filling:
  • 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
  • a few drops of green food coloring
  • green sparkling sugar for decorating

Instructions

  • 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 minutes (we always did this at Baked, 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 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 like extra . . .

These grasshopper whoopie pies are cake-like … how about some cake recipes?

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