11 months ago

Chocolate Peppermint Whoopie Pies

Two soft, cake-like cookies sandwiched around mounds of fluffy peppermint filling! A must-try holiday cookie recipe from Twin Cities food blogger greens & chocolate.

Is anyone else excited for baking season? I absolutely love this time of year for so many reasons – the lights, the decorations, the parties, and of course the baking! There’s nothing I love to do more on the day of the first snowfall than to get in my cozy clothes, turn on some Christmas music (don’t hate me for loving Mariah Carey) and whip up some cookies.

I definitely have a list of the things I try to make every year like my perfectly chewy sugar cookies, ginger molasses cookies, saltine toffee and the peanut butter kiss cookies, but I also save some butter for new recipes, too!

One of my favorite flavor combinations around the holidays is peppermint and chocolate. Enter: Chocolate Peppermint Whoopie Pies.

While there are lots of recipes called “whoopie pies” with chewy cookies, whoopie pies are traditionally soft, cake-like cookies filled with a fluffy filling. This recipe definitely is more on the traditional side as I made a chocolate cookie that is very cake-like.

In between the two soft cookies, I slathered a sizable amount of peppermint filling. To me, the more frosting, the better. These whoopie pies are essentially a meal in itself so bring. on. the. frosting. Come to think of it, they’re almost like individual cakes with the frosting on the inside. A hand-held cake! What more could you want?

A couple of notes about these cookies. Since the cookies are soft, they don’t do well stacked on each other. So I wouldn’t recommend stacking them in Tupperware containers unless you want them sticking to each other. Which I doubt you do.

I would also recommend storing them in the refrigerator for up to 3 days in an airtight container.

So what’s on your baking list this holiday season? Maybe these Chocolate Peppermint Whoopie Pies?  They would be the star of any holiday cookie platter!

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Chocolate Peppermint Whoopie Pies

Makes about 20 whoopie pies
Preparation time: 50 minutes (not including time for cookies to cool)

Ingredients

For the cookies:

  • 1 ⅔ cup all-purpose flour
  • ⅔ cup unsweetened cocoa powder
  • 1 ½ teaspoons baking soda
  • ½ teaspoon salt
  • ½ cup unsalted butter
  • 1 cup packed brown sugar
  • 1 egg
  • 1 teaspoon vanilla extract
  • 1 cup milk

For the filling:

  • 1 cup unsalted butter, at room temperature
  • 2 cups powdered sugar
  • 1 cup marshmallow fluff
  • 2 tablespoons milk
  • 1 teaspoon peppermint extract
  • Red food coloring
  • Crushed candy canes

Directions

For the cookies:

  1. Heat oven to 375 F.
  2. Line baking sheets with parchment paper.
  3. In a medium bowl, add flour, cocoa, baking soda and salt; mix until combined.
  4. In separate large bowl, beat butter and sugar with a mixer on medium until light and fluffy, about 2 minutes.
  5. Add egg and vanilla and beat for two more minutes.
  6. Add half of the flour mixture and half of the milk and beat on low until incorporated.
  7. Repeat with remaining flour and milk and beat until combined.
  8. Drop batter on prepared baking sheets in tablespoon clumps, each about two inches apart. Bake for 10-12 minutes each or until pies spring back when pressed gently.
  9. Cool for about five minutes before transferring them to a rack to cool completely.

For the filling:

  1. In a large bowl with electric mixer, beat together butter and powdered sugar until light and fluffy, about 2 minutes.
  2. Add marshmallow fluff, milk and peppermint extract; beat another 2 minutes.
  3. Remove about half of the filling that will remain white.
  4. Add a few drops of red food coloring to the remaining filling and beat until combined. Add more until desired color is attained.
  5. Spread or pipe filling onto half of the cookies. Top with remaining cookies.
  6. Place crushed candy canes in a shallow bowl or on a plate and roll the cookie filling in crushed candy canes.

Serve and enjoy!