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Makin’ Whoopie Pies

Author Photo
By Andrew Weidman | Oct 6, 2020

 
Photo by Adobe Stock/Alp Aksoy

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!”

 

Peanut-Butter-Filled Whoopie Pie. Photo by Andrew Weidman

Mom’s Traditional Chocolate Whoopie Pie or Peanut-Butter-Filled Whoopie Pie Recipe

Yield: about 24 pies.

Cookie 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 ingredients

  • 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

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.

Note: For peanut butter whoopie pies, exchange butter in filling recipe with 1/2 cup creamy peanut butter for maximum peanut butter flavor.


 

Pumpkin Whoopie Pie. Photo by Andrew Weidman 

Pumpkin Whoopie Pie Recipe

Yield: about 24 pies.

Cookie ingredients

  • 2-1/4 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1 tablespoon ground cinnamon
  • 1-1/2 teaspoons ground ginger
  • 1 teaspoon ground allspice
  • 1 teaspoon ground nutmeg
  • 1/2 teaspoon salt
  • 1 cup brown sugar
  • 1/2 cup butter, at room temperature
  • 1-1/2 cups solid pack pumpkin
  • 1 egg
  • 1 teaspoon vanilla extract

Filling ingredients

  • 4 ounces cream cheese, at room temperature
  • 4 tablespoons butter, at room temperature
  • 3-1/2 cups powdered sugar
  • 1 teaspoon vanilla extract

Directions

  1. Preheat oven to 350 F. Using a whisk, blend together flour, baking powder, baking soda, cinnamon, ginger, allspice, nutmeg, and salt in a large bowl. In the work bowl of a stand mixer fitted with the paddle attachment, beat together brown sugar and butter on low speed until just combined. Add pumpkin, and then egg, beating well. Add vanilla, and beat until combined. Add flour mixture, and beat on low until just incorporated, scraping down the sides of the bowl with a spatula. Drop mixture by teaspoons or tablespoons (depending on the cookie size you’d like to create) onto parchment-lined cookie sheets. Bake for 15 minutes each, or until cookies begin to crack and are firm to the touch. Let cookies cool on sheet for at least 3 minutes before transferring to a rack to cool completely.
  2. In the work bowl of a stand mixer fitted with a paddle attachment, beat together cream cheese and butter on medium speed. Add sugar, and beat on low speed until combined. Add vanilla, and increase speed to medium; beat until creamy and smooth, about 4 minutes.
  3. Spread filling on flat side of a completely cooled cookie, and sandwich with a second cookie. For teaspoon-sized pies, use 1 teaspoon filling per sandwich; for larger pies, use 1 tablespoon filling per sandwich.

 
Inside-Out Whoopie Pie. Photo by Andrew Weidman

Inside-Out Whoopie Pie Recipe

Yield: about 24 pies.

Cookie ingredients

  • 2-1/4 cups all-purpose flour
  • 1-1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 4 tablespoons butter, at room temperature
  • 4 tablespoons shortening
  • 1/2 cup granulated sugar
  • 1/2 cup brown sugar, packed
  • 2 large eggs
  • 1/2 cup buttermilk
  • 2 tablespoons whole milk
  • 1 teaspoon baking soda
  • 1 teaspoon white vinegar
  • 1 teaspoon vanilla extract

Ganache Filling ingredients

  • 1 pound bittersweet chocolate, chopped
  • 2-1/2 cups heavy whipping cream
  • Pinch of salt
  • 1 tablespoon vanilla extract, rum, or rose water (my wife prefers using Godiva Chocolate Liqueur)

Directions

  1. Preheat oven to 375 F. Using a whisk, blend together flour, baking powder, and salt in a medium bowl. In the work bowl of a stand mixer fitted with a paddle attachment, beat together butter, shortening, and both sugars until light and creamy, about 3 minutes. Add eggs and buttermilk, and beat until combined. Combine milk, baking soda, and vinegar in a measuring cup. Add milk mixture to batter along with flour mixture, and beat on low until just combined. Add vanilla, and beat on medium for about 2 minutes until completely combined. Using a spoon, drop about 1 tablespoon of batter onto parchment-lined cookie sheets. Repeat, spacing them out at least 2 inches apart. Bake about 10 minutes, or until cookies begin to brown. Remove from oven and allow to cool 3 minutes before transferring to cooling rack.
  2. Place bittersweet chocolate in a large heat-proof bowl. In a large, heavy-bottomed saucepan, heat cream over medium heat until it bubbles. Pour hot cream over chopped chocolate, and let sit for about 10 minutes, until chocolate is melted. Add salt and vanilla (or substitute), and stir with a wooden spoon or silicone spatula to just combine.
  3. Refrigerate ganache for at least 1 hour (up to 24 hours) until firm. Using a hand mixer or stand mixer, beat ganache at medium speed until softened and lighter in color, about 2 minutes.
  4. Spread filling on flat side of a completely cooled cookie, and sandwich with a second cookie. For teaspoon-sized pies, use 1 teaspoon filling per sandwich; for larger pies, use 1 tablespoon filling per sandwich.

 

Tiramisu Whoopie Pie. Photo by Andrew Weidman 

Tiramisu Whoopie Pie Recipe

Yield: about 24 pies.

Cookie ingredients

  • 3 tablespoons instant espresso powder or instant coffee
  • 2 tablespoons water
  • 2-1/4 cups all-purpose flour
  • 1/2 cup unsweetened dark cocoa powder
  • 1-1/2 teaspoons baking soda
  • 1/2 teaspoon salt
  • 4 tablespoons butter, at room temperature
  • 4 tablespoons shortening
  • 1 cup packed dark-brown sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 cup whole milk

Filling ingredients

  • 1/2 cup mascarpone cheese, at room temperature
  • 4 tablespoons butter, at room temperature
  • 3 cups powdered sugar
  • 1 tablespoon espresso, strong-brewed coffee, or instant espresso powder (for stronger coffee flavor)
  • 1/2 teaspoon vanilla extract
  • 1 teaspoon rum or Marsala (optional)

Directions

  1. Preheat oven to 375 F. In a small bowl or cup, mix instant espresso powder and water. Set aside.
  2. In a medium bowl, whisk together flour, cocoa powder, baking soda, and salt. In the work bowl of a stand mixer fitted with a paddle attachment, beat together butter, shortening, and brown sugar on low speed until just combined. Increase speed to medium, and beat mixture until fluffy and smooth, about 3 minutes. Add egg and vanilla, and beat for another 2 minutes. Add half the flour mixture and half the milk, and beat on low until just incorporated. Scrape down the sides of the bowl. Add espresso-water mixture and remaining flour mixture and milk, and beat until completely combined.
  3. Using a spoon, drop 1 tablespoon of batter onto parchment-lined cookie sheets and repeat, spacing them at least 2 inches apart. Bake for about 10 minutes, or until the cookies spring back when touched. Remove from oven and let cool for about 3 minutes; then transfer to cooling rack.
  4. In the work bowl of a stand mixer fitted with a paddle attachment, beat together mascarpone and butter. Add sugar, and beat on low speed. Increase speed to medium and beat until fluffy, about 3 minutes. Add espresso, vanilla, and optional rum; beat until combined.
  5. Spread filling on flat side of a completely cooled cookie, and sandwich with a second cookie. For teaspoon-sized pies, use 1 teaspoon filling per sandwich; for larger pies, use 1 tablespoon filling per sandwich.

Refrigerate whoopie pies in single layers on waxed paper or wrapped in plastic wrap to prevent them from sticking together. They can also be frozen for long-term storage — and to protect treats intended for gatherings from grazing family members.

Get Baking! Want to make more kinds of whoopie pies? Spice up the holidays with Gingerbread Whoopie Pies with Lemon Crème.


Andrew Weidman lives and writes in the heart of Pennsylvania Dutch Country. The Traditional Chocolate Whoopie Pie and Peanut-Butter-Filled Whoopie Pie recipes are courtesy of the late Beatrice Weidman.

 

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