Chocolate Peppermint Whoopie Pies

This past week, my girls and I baked our first Christmas cookies of the season. After seeing whoopie pies in a book we read before Thanksgiving, my girls were eager to try some.

These did not disappoint! If you have time to make these delightful cookies, then add them to your baking list. Those eating your cookies will be delighted by their appearance and flavor!

Ingredients

(Adapted from this recipe.)

For the cookies

• 2 cups all-purpose flour
• ½ cup cocoa powder
• 1 ½ teaspoons baking soda
• ½ teaspoon baking powder
• ½ teaspoon fine salt
• 1 cup granulated sugar
• 8 tablespoons (1 stick) butter, at room temperature
• 1 large egg
• 1 teaspoon vanilla extract
• 1 teaspoon peppermint extract
• 1 cup milk

For the filling

• 2 cups confectioners’ sugar
• 8 tablespoons (1 stick) butter, at room temperature
• 1 cup marshmallow creme
• 1 teaspoon peppermint extract
• ½ teaspoon vanilla extract
• 1-2 tablespoons milk
• 4-6 candy canes, crushed
• Candy cane sprinkles or additional crushed candy canes

Instructions

For the cookies

In a large bowl, stir together the flour, cocoa, baking soda, baking powder, and salt.

In another large bowl, beat together the granulated sugar and butter. Beat in the egg and the extracts. Alternate adding the dry mixture and the milk (begin and end with the dry mixture). Mix until just incorporated. Refrigerate the dough for 1 hour.

Preheat the oven to 400°F. Line a baking sheet with parchment paper. Drop tablespoonfuls of the batter about 3 inches apart on the prepared baking sheet. Do not crowd because the batter will spread slightly as it bakes. Return the remaining batter to the fridge until you are ready to bake it.

Bake for 7 minutes or until the cookies puff up and the tops are no longer glossy. Allow to cool for a few minutes on the baking sheet, then transfer to a wire rack to cool completely (about 1 hour). Let the baking sheet cool, then bake the remaining batter in batches (allow the baking sheet to cool each time).

For the filling

In a large bowl, beat the confectioners’ sugar and butter. Add the marshmallow crème and extracts. Continue beating until light and airy. If the filling is too stiff, then add the milk a little at a time (if the filling is too runny, then add a little more confectioners’ sugar instead). Gently stir in the 4-6 crushed candy canes.

Spread a dollop of the filling on half of the cookies. Sandwich these with the remaining halves, pushing down gently to move the filling to the edges. Place the candy cane sprinkles (or the additional crushed candy cane) onto a plate and carefully roll the sides of the whoopie pies in the sprinkles or candy. Yield: about 20 whoopie pies.

Notes

I have a love-hate relationship with these cookies. I love them because they are delicious, they look amazing, and they are fun to eat. On the other hand, I hate them because they take a lot of work to prepare (the dough must be chilled and you can only bake a few of the cookies at a time, plus you must make the filling and roll the assembled cookies in sprinkles or crushed candy). It takes about 3 ½ hours to prepare these from start to finish. Was it worth it? Yes, because my kids enjoyed making and eating them. However, we probably won’t make them every Christmas.

With that being said, I will keep the recipe in mind because these would be perfect for a bake sale or baking contest. They are very tasty, and they have a wonderful, festive appearance. Additionally, there is a lot of room for experimentation with this recipe. A chocolate cherry version would be delightful, as would a s’more version. Someday I may give these a try.

In the meanwhile, I’d love to hear what you are baking! What cookies have you made this holiday season?

Shared at the following:

Homestead Blog Hop, Weekend Potluck, Busy Monday, and Encouraging Hearts and Home.