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Stack of peppermint sandwich cookies with milk in the background.
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4 from 1 vote

Chocolate Peppermint Sandwich Cookies

Soft chocolate cookies sandwiching peppermint frosting and rolled in crushed peppermint candies. A festive cookie for the holidays!
Course Cookies, Dessert
Cuisine American
Prep Time 25 minutes
Cook Time 10 minutes
Total Time 35 minutes
Servings 14 sandwich cookies (cookies can be made smaller which would produce a higher yield)
Calories 354kcal

Ingredients

Cookies:

  • 4 tablespoons unsalted butter cubed
  • 1/2 cup semisweet chocolate chips
  • 1 cup brown sugar
  • 3 large eggs
  • 1 cup all purpose flour
  • 1/2 cup unsweetened cocoa powder
  • 1 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt

Filling:

  • 8 tablespoons unsalted butter softened
  • 2 cups powdered sugar
  • 2 teaspoons milk
  • 1/4 teaspoon peppermint extract or more to taste
  • 1/3 cup crushed candy canes or peppermint candies

Instructions

Cookies:

  • Preheat oven to 325°F and line two baking sheets with parchment paper or silicone liners.
  • In a small saucepan over medium-low heat, melt 4 tablespoons of butter and chocolate chips until completely smooth. Set aside to cool for 10 minutes.
  • Meanwhile, in a large bowl whisk brown sugar and eggs. Set aside.
  • In a separate bowl, whisk flour, cocoa powder, baking powder, baking soda, and salt.
  • Pour the melted chocolate mixture into the eggs and brown sugar and whisk until combined. Add the flour mixture and stir until combined (I stir it with a rubber spatula). The dough will be sticky, but if it seems too wet to scoop, mix in another tablespoon or two of flour. 
  • Scoop dough by the tablespoon (I use a scoop) and place 2 inches apart on prepared baking sheets. Dampen your palm, and lightly press down on each mound of dough to flatten slightly. Bake for 9-10 minutes, until the edges are set and the centers are puffed and still appear slightly underdone (they will continue to cook as they cool). Place baking sheets on cooling racks and cool completely.

Filling:

  • Using a hand mixer or stand mixer, beat butter until smooth. Add powdered sugar and beat until combined. Add milk and peppermint extract and beat on medium speed for 1 minute, until smooth and creamy.
  • Using a butter knife or pastry bag, spread or pipe frosting onto the bottom of half the cookies. Top with the remaining cookies. If desired, roll the edges (where the frosting is) in crushed candy canes.

Notes

I made these cookies with 1 1/2 tablespoons of dough, which made a dozen 3-inch cookies. If you'd like your cookies a little smaller, feel free to do so. Just adjust the baking time accordingly, reducing it by several minutes. Be sure not to overbake; the cookies should be soft.

Nutrition

Calories: 354kcal | Carbohydrates: 52g | Protein: 3g | Fat: 15g | Saturated Fat: 9g | Cholesterol: 71mg | Sodium: 96mg | Potassium: 181mg | Fiber: 2g | Sugar: 40g | Vitamin A: 410IU | Calcium: 51mg | Iron: 1.8mg