Chocolate Peppermint Whoopie Pies

Love chocolate and peppermint? You'll love these sweet, delicate Chocolate Peppermint Whoopie Pies!

For this month’s cookie of the month, I feel like I’m cheating a little bit. Whoopie pies always make me think of cookies. They look and eat like a cookie, but they have a consistency similar to cake. To confuse the situation further, they’re called pies. Go figure.

Regardless of the technicalities of their classification, I assure you they are delicious. These beauties consist of dark chocolate, cake-like cookies filled with a peppermint cream cheese frosting.

Peppermint and chocolate are a perfect pair in these lovely, delicate, delicious Chocolate Peppermint Whoopie Pies! - Bake or Break

The recipe for these comes to us from One Girl Cookies, a lovely bakery with a very handy (and dangerous!) location in my neighborhood. They always have whoopie pies tempting me from their display case. Their usual chocolate whoopie pies have traditional cream cheese frosting, but this peppermint variety is a holiday favorite in their cookbook.

I normally hesitate to bake anything that requires piping batter or frosting. It’s just not my favorite thing. And truth be told, I’m not very good at it. If you don’t take away anything else from this, here’s what I want you to know. Even with my mediocre piping skills, these little guys always turn out beautifully. They are very forgiving. Believe me, they don’t go into the oven looking nearly as good as the finished product.

Through some sort of baking magic, these cookies turn from lumpy, misshapen blobs into beautiful cookies. Then just fill them with frosting, whether it be this peppermint frosting or your favorite variety. When you serve these to your friends, you’ll be a baking rock star!

These cookies are my contribution to Cookie of the Month, a monthly group of cookie recipes from some of my blogging friends and me. This month’s theme is mint. Be sure to visit these ladies’ blogs to see their mint cookie creations!

Catch up with the previous Cookies of the Month with Cherry-White Chocolate Oatmeal Cookies and Fudgy Kahlua Brownie Cookies.

Chocolate Peppermint Whoopie Pies

Yield: 24 whoopie pies

Prep Time: 25 minutes

Cook Time: 10 minutes

Ingredients:

For the cakes/cookies:

  • 2 cups all-purpose flour
  • 1/2 cup Dutch-processed cocoa powder, sifted
  • 3/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup granulated sugar
  • 1/2 cup firmly packed light brown sugar
  • 1/2 cup plain full-fat yogurt*
  • 1/3 cup canola oil
  • 3 large eggs
  • 1 teaspoon vanilla extract

For the filling:

  • 4 ounces cream cheese, softened
  • 5 tablespoons unsalted butter, softened
  • 1/2 teaspoon peppermint extract
  • 1/8 teaspoon salt
  • 2 & 1/2 to 3 cups confectioners’ sugar, sifted**

Directions:

*To make the cakes/cookies:*

Whisk together the flour, cocoa powder, baking soda, and salt. Set aside.

Using an electric mixer on medium speed, beat the sugar, brown sugar, yogurt , oil, eggs, and vanilla until thoroughly combined and smooth (about 3 minutes).

Reduce the mixer speed to low. Gradually add the flour mixture and mix just until combined. Refrigerate the batter for 30 minutes.

Preheat oven to 350ยฐ. Line a baking sheet with parchment paper.

Using a pastry bag with a large plain tip or a plastic bag with the corner snipped, hold the bag vertically and very close to the parchment paper, and pipe the batter in 2-inch circles onto the prepared pan. Leave about 1 & 1/2 inches between each.

Bake for 10 minutes, or until the centers spring back when touched. Repeat with remaining batter, baking one sheet at a time. Cool the whoopie pies completely.

To make the filling:

Using an electric mixer on medium speed, beat the cream cheese and butter until light and fluffy. Add the peppermint and salt, and mix well.

Reduce the mixer speed to low. Gradually add the confectioners’ sugar, and mix well.

To assemble the whoopie pies:

Turn half of the whoopie pies so that the bottoms face upward. Pipe or spread 1 to 1 & 1/2 tablespoons of filling on each. Top with the remaining whoopie pies.

Notes:

*Confession: I tend to use the yogurt I always have on-hand, which is a non-fat vanilla yogurt. It works just fine.

**I like my cream cheese frosting a little less sweet than most. If you like yours on the sweeter side, use the full 3 cups of confectioners’ sugar.