Double Chocolate Peppermint Whoopie Pies


It’s the most wonderful time of the year…errr…month…err…today is doubly wonderful!

That’s right, folks. Not only does December usher in the season of ribbons and lights and hot cocoa, it also means it’s time for another chocolate party!

Today wins. Clearly.

This month the theme was chocolate and mint. It’s an obvious choice for the season.

Warm and cozy chocolate comforts like a spot by the fireplace while mint gives just a hint of winter’s chill.

The only problem with this theme is all the decisions it required. I happen to be terrible at making decisions, especially when it comes to food, and ESPECIALLY when it comes to really good food. How am I supposed to decide between peppermint or spearmint, candy canes or Andes, cakes or cookies? There are just way too many fantastic possibilities.

It was nearly a crisis, but after much deliberation, anxious sweating, and tears (ok, it wasn’t quite THAT bad), I finally settled on something. Chocolate Peppermint Whoopie Pies.

They’re the best of compromises. Part cake and frosting, part cookie, and spiked with just the right amount of peppermint extract and candy cane pieces for a cool, creamy treat.

I used my go-to recipe for the whoopie pie cakes. They’re dependably puffy and have just the right amount of chocolate flavor. But these whoopie pies needed something extra special for the filling. Something sparkly, something creamy, something fresh, and…what the heck…why not throw some more chocolate in there too?

So here it is. Chocolate whoopie cakes sandwiched around a fluffy chocolate mint cream filling, then rolled in crushed peppermint. It’s sweet, it’s refreshing, it’s cozy, it’s festive.

It’s the most wonderful time of the year…and month…and day.

Be sure to check out all these other great options for all your Christmas festivities as well!

Double Chocolate Peppermint Whoopie Pies
 
Prep time
Cook time
Total time
 
Serves: 36
Ingredients
For the cookies:
  • 1 cup shortening
  • 2 cups sugar
  • 2 eggs
  • 5 cups flour
  • ¾ cup cocoa
  • 1½ teaspoons salt
  • 1 cup milk
  • 1 Tablespoon vinegar
  • 1 cup hot water
  • 2 teaspoon soda
For the filling:
  • 1 cup shortening
  • 1 cup powdered sugar
  • 1⅓ cups marshmallow creme
  • 4 oz. unsweetened chocolate, melted
  • ¼ teaspoon salt dissolved in 1 Tablespoon water
  • 1 teaspoon vanilla extract
  • 1 teaspoon peppermint extract
  • 2 Tablespoons-1/4 cup milk
  • 3-4 candy canes or peppermint mints
Instructions
For the cakes:
  1. Preheat oven to 400 degrees. Line 2 large baking sheets with parchment paper.
  2. In the bowl of an electric mixer, beat eggs. Add shortening and sugar and beat until fully combined and fluffy. In a large bowl, whisk together flour, cocoa, and salt. In another small bowl or measuring cup, mix together vinegar and milk.
  3. With the mixture on low speed, add flour mixture to shortening mixture, a little at a time, alternating with the milk, stirring until combined.
  4. Dissolve the baking soda in hot water. Add it to the cookie dough and beat until smooth.
  5. Drop heaping Tablespoons of dough onto the parchment paper, leaving about an inch of space between each one.
  6. Bake in the preheated oven for 6-8 minutes or until cookies are firm to the touch. Allow to cool on the baking sheets for a few minutes then remove and cool completely.
For the filling:
  1. Beat together the shortening, sugar, and marshmallow creme. Beat in melted chocolate. Stir in vanilla and peppermint extract. Mixture will be very thick. Beat in milk until mixture is just thin enough to spread easily.
To assemble:
  1. Crush the peppermint using a food processor or small hammer. Place into a shallow bowl.
  2. Spread cream mixture between two cookies. Press the cookies down until the filling reaches the edges. Roll the edges in the crushed peppermint. Serve or store in the fridge. Candy canes will start to melt after awhile, so the sooner you can eat these babies the better!
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