Chocolate Whoopie Pies with Peppermint Frosting

It’s Christmas Eve and possible that you may still be looking for a festive, impressive, but easy dessert to pass around. My family is pretty evenly split between cake lovers and pie lovers, but the one thing we can all agree on is that whoopie pies (the kind with lots of frosting) are always welcome to make an appearance, especially around the holidays. Last year for Thanksgiving I made these Pumpkin Whoopie Pies with Maple Frosting and they disappeared immediately.  Not quite a cake, not quite a cookie, they’re more like the best of both. This year I went with a classic chocolate whoopie pie with a peppermint buttercream frosting. Roll them in some crushed peppermint candies if you’re serving them to guests, and watch what I mean about disappearing.

Sift together all the dry ingredients- the flour, cocoa powder, baking soda and salt in a medium sized mixing bowl and set aside.

     

Beat together the brown sugar, softened butter and shortening until fluffy and smooth, starting slow and gradually building up speed, about 4 minutes. Add in the egg and vanilla and beat for another 2 minutes.

Add in half the flour mixture and half of the milk and mix until just combined. Repeat with the remaining flour mixture and milk.

     

Drop rounded tablespoons of batter onto cookie sheets, spacing a couple of inches apart. Bake 1 sheet at a time at 375 in the center of the oven for 10 minutes. The pies should spring back when pressed gently.

Let the whoopie pies cool on the hot sheets for 5 minutes before transferring to a wire rack to cool completely.

     

Prepare the peppermint buttercream frosting while the pies are cooling. Beat together the powdered sugar and softened butter, starting on low speed and increasing to medium, until the mixture is crumbly, about 1 minute. Add in the heavy cream, vanilla, peppermint extract and salt and beat on high until smooth, about 3 minutes. Be sure you’re using peppermint extract and not mint extract. You don’t want the frosting to taste like toothpaste.

Once the frosting is thick and creamy, frost the flat side of one of your whoopie pies. Use a spoon or knife, or a pastry bag if you want a more polished look. Be generous with your frosting. If your treat is flat or thinly filled, I’m sorry to say that is not a proper whoopie pie. Top with the remaining halves.  When I make these Christmas whoopie pies, I like to decorate the sides by rolling them in crushed peppermint candies or candy canes. Use festive sprinkles or chocolate chips or even keep them plain if you prefer.

It’s best to eat whoopie pies within a few days, as they can be challenging to store. They tend to stick to each other when stacked, so if you need to store them for a few days, try and find a shallow, wide container in which they can lie flat. If you do need to stack them, no big deal, just be sure to place waxed paper between the layers to avoid sticking. You can also wrap the whoopies individually in plastic wrap. Store for up to 3 days in an airtight container at room temperature.

If you are planning on freezing the pies, transfer them to a cookie sheet, and freeze for 1 hour until they are solid. Once solid, you can wrap them individually in plastic wrap, then place them into a large freezer bag. Freeze for 30-45 days.

Chocolate Whoopie Pies with Peppermint Frosting
Chocolate Whoopie Pies with Peppermint Frosting- not quite a cake, not quite a cookie, it's more like the best of both.
Servings
20 pies
Cook Time
20 minutes
Servings
20 pies
Cook Time
20 minutes
Chocolate Whoopie Pies with Peppermint Frosting
Chocolate Whoopie Pies with Peppermint Frosting- not quite a cake, not quite a cookie, it's more like the best of both.
Servings
20 pies
Cook Time
20 minutes
Servings
20 pies
Cook Time
20 minutes
Ingredients
Chocolate Whoopie Pies
  • 1 2/3 cup flour
  • 2/3 cup cocoa powder unsweetened
  • 1 1/2 tsp baking soda
  • 1/2 tsp salt
  • 4 tbsp butter unsalted, room temperature
  • 4 tbsp shortening
  • 1 cup brown sugar packed
  • 1 egg
  • 1 tsp vanilla
  • 1 1/4 cups milk
Peppermint Frosting
  • 4 cups powdered sugar
  • 8 tbsp butter unsalted, room temperature
  • 6 tbsp heavy whipping cream
  • 4 tsp vanilla
  • 1 tsp peppermint extract
  • 1 tsp salt
Instructions
  1. Position a rack in the center of the oven and preheat to 375. Line two cookie sheets with parchment paper or silicone mats. Set aside.
  2. Sift together the flour, cocoa powder, baking soda and salt in a medium sized mixing bowl. Set aside.
  3. In the bowl of an electric mixer fitted with the paddle attachment, beat together the butter, shortening and brown sugar on low speed until just combined. Increase the speed to medium and beat until fluffy and smooth, about another 2 minutes.
  4. Add in the egg and vanilla and beat for another 2 minutes.
  5. Add half of the flour mixture and half of the milk to the batter and beat on low until just incorporated. Scrape down the sides of the bowl is necessary. Add in the remaining flour mixture and milk and beat until combined.
  6. Using a spoon or cookie scoop, drop about 1 rounded tablespoon of batter onto one of the the prepared baking sheets and repeat, spacing 2 inches apart.
  7. Bake one sheet at a time for about 10 minutes each, or until the pies spring back when pressed gently.
  8. Remove from the oven and let cool on the hot sheet for 5 minutes before transferring to a wire rack to cool completely.
  9. While cakes are cooling, prepare your frosting. In the bowl of an electric mixer fitted with the paddle attachment, beat together the powdered sugar and softened butter, starting on low speed and increasing to medium, until the mixture is crumbly, about 1 minute.
  10. Add in the cream, vanilla, peppermint extract and salt and beat on high until smooth, about 3 minutes.
Recipe Notes

Store whoopie pies in an airtight container at room temperature for up to 3 days. If wrapped individually, they can be frozen for up to 1 month.

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