Making Whoopie Pies

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Adobe Stock/Alp Aksoy
24 SERVINGS

Ingredients

  • 1 cup shortening
  • 2 cups sugar
  • 2 eggs
  • 1 cup whole milk, soured with 1 teaspoon vinegar
  • 2 teaspoons vanilla extract
  • 4 cups flour
  • 1 cup dark cocoa powder
  • 1 teaspoon baking powder
  • 2 teaspoons salt
  • 1 teaspoon baking soda
  • 1 cup hot water

Filling

  • 1 cup whole milk
  • 4 tablespoons flour
  • 1/4 pound butter, softened
  • 1-1/2 cups shortening
  • 3 cups powdered sugar
  • 1 teaspoon vanilla extract

Directions

  • Preheat oven to 400 F. In a large bowl, cream shortening and sugar, add eggs, and combine. Add milk and vanilla, and beat again until smooth and thoroughly combined. In a separate bowl, mix flour, cocoa, baking powder, and salt. Mix these ingredients together with a dry whisk, being sure to break up any larger cocoa powder lumps. If small cocoa lumps remain, they’ll mix into the wet ingredients.
  • Add dry mixture to wet mixture, and combine thoroughly with a hand mixer or stand mixer, about 2 minutes on medium speed. Mix baking soda into hot water, add to batter, and mix until batter is thoroughly blended together and smooth.
  • Drop mixture by teaspoons or tablespoons (depending on the cookie size you’d like to create) onto parchment-lined cookie sheets. Bake 8 to 10 minutes. If you used a teaspoon for the cookies, check them at 8 minutes. The cookies are finished when your finger no longer leaves a dent in the top when pressed lightly. Let stand for 1 to 2 minutes on the parchment-lined cookie sheet, and then remove carefully by hand and place on the cooling rack.
  • While cookies are cooling, combine milk and flour for the filling in a small saucepan. Cook over medium heat, whisking constantly until mixture boils and thickens to the consistency of creamy peanut butter. Remove from heat, and allow to cool on a cooling rack. Once cooled completely, combine with butter, shortening, powdered sugar, and vanilla in a mixing bowl. Beat for 5 minutes until smooth.
  • Spread filling on flat side of a completely cooled cookie, and sandwich with a second cookie. For teaspoon-sized pieces, use 1 teaspoon filling per sandwich; for larger pies, use 1 tablespoon filling per sandwich.
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Are you ready? We’re making whoopie today! Whoopie pies, that is. Let’s start with what they aren’t: a pie. Yes, I know, it’s in the name. No, I don’t know why. What I do know is that whoopie pie is a mouthwatering Pennsylvania Dutch Country treat. It’s a staple at bake shops, farmers market bakery stands, and even convenience store checkout counters.

Picture two chocolate sugar cookies, so dark they’re nearly black, and so soft they’re more like little cakes, sandwiching a layer of white vanilla filling. That’s the traditional whoopie pie. No need to stop at that, though. Some variations of classic whoopie pies include peanut-butter-filled whoopies, pumpkin whoopies with cream cheese filling, inside-out whoopies with vanilla cake cookies and chocolate ganache filling, and tiramisu whoopies. And that’s still just the beginning; the possibilities are endless. What better way to serve cake at a family reunion or backyard barbecue, or slip a piece of cake into a lunchbox without getting icing everywhere?

In fact, that’s where the name “whoopie pie” comes from. According to local legend, Amish mothers slipped whoopie pies into their children’s lunchboxes for a midday surprise. The kids would be so overwhelmed with excitement at discovering this chocolaty treat, they couldn’t help but shout, “Whoopie! Look what I’ve got!” Is that true? Try one and decide for yourself.

In western Pennsylvania’s coal country, these treats go by the name “gobs,” maybe because they reminded miners of black lumps of coal, also called “gobs.” One could even argue that a moon pie, a treat that originated in Tennessee, is a type of whoopie pie. In Maine, one of the first records of a whoopie pie — its official state treat — can be found in a 1930s recipe book titled The Yummy Book. In 1926, New York bakers began marketing an oblong cookie sandwich of devil’s food cake and white cream, called the “devil dog.” Meanwhile, the Amish and Mennonite bakers of south-central Pennsylvania kept quietly baking their own whoopie pies, slipping them into their families’ lunch kettles and selling them at farmers’ markets.

Who had it first? It’s hard to say with any certainty. However, the Amish have their roots in the early Mennonite church in Pennsylvania, and the Mennonites, in turn, immigrated to colonial Pennsylvania from 1700s Germany, where cream-filled cake recipes can be found.

I guarantee that when your family finds these treats in their lunchboxes or at a picnic, they won’t care who had it first. They’ll be too busy shouting, “Whoopie!”

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