These Chocolate Peppermint Sandwich Cookies will be the star of your next cookie swap

My daughter, Maggie, has loved to bake since she was a little girl. Because of that, my family has always relied on her to create something special for our holiday dessert table and to leave out for Santa. 

A couple of Christmases ago, Maggie perfected her Chocolate Peppermint Sandwich Cookie, and it has been a new family favorite ever since. This rich chocolate cookie with a slight hint of mint is filled with a sweet, creamy vanilla and peppermint buttercream and topped with crushed candy canes. 

This special holiday cookie is fun to make, and a treat to eat and share with friends and family. Not to mention, Santa now requests this cookie every year.

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Maggie’s Chocolate Peppermint Sandwich Cookies

For the cookies:

½ cup butter

9 oz chocolate chips (or chopped chocolate)

1 ¾ cups AP flour

¼ cup Dutch process cocoa powder or Hersey’s Special Dark Cocoa Powder

1 tsp baking powder

1 tsp baking soda

½ tsp salt

3 large eggs

½ cup light brown sugar

1 cup granulated sugar

1 tbsp vanilla extract

1. In a heavy saucepan over low heat, add the butter and chocolate, stirring often until the chocolate and butter melts. Once melted, remove from heat, and stir until smooth. Pour the melted chocolate and butter mixture into the bowl of a stand mixer fitted with a paddle attachment and allow to cool slightly. 
2. In a separate bowl, whisk together flour, cocoa powder, baking powder, baking soda and salt. Set it aside.
3. Once the chocolate mixture has cooled slightly, add the eggs, light brown sugar and granulated sugar into the bowl of a stand mixer. Mix on a medium-low speed until well combined. Add the vanilla and mix until just combined. 
4. Add the dry ingredients to the chocolate mixture. Mix until fully incorporated 
5. Cover the bowl with plastic wrap and chill for 30-45 minutes. 
6. Preheat the oven to 350 F, line two baking sheets with parchment paper and set aside. 
7. Remove the chilled dough from the fridge and use a small cookie scoop to measure out the cookie dough. Roll each cookie dough scoop in your hands to create a ball. Place the dough balls on the prepared cookie sheet about 2 inches apart.
8. Bake for 8-10 minutes or until the edges are set and the center of the cookies begin to puff. The cookies should look slightly cracked.
9. Remove the cookies from the oven and allow them to cool on the baking sheet for 8-10 minutes before transferring to a wired rack to cool completely.

For the peppermint frosting:

¾ cups softened butter

4 cups powdered sugar

2 teaspoons pure vanilla extract

¼ to ½ teaspoon pure peppermint extract

2 teaspoons milk

1. Place the softened butter into the bowl of a mixer fitted with the paddle attachment, and begin whipping the butter on high speed until light and fluffy.
2. Reduce the speed to low and begin adding the powdered sugar 1 cup at a time making sure each cup is fully incorporated. The mixture will be very thick at this point.
3. Add in the vanilla extract, peppermint extract and milk and bump the speed up to medium. Continue whipping the frosting 3 to 4 minutes until the fluffy. 
4. Make sure the cookies are completely cool before assembling the cookie sandwiches. To make the sandwiches, pipe a swirl of peppermint frosting onto the flat side of the cookie. Top with the flat side of another cookie and gently press together. 

To decorate the Chocolate Peppermint Sandwich Cookies:

4 ounces chocolate chips or chopped chocolate, melted

12 crushed peppermint candies or candy canes

1. Melt the dark chocolate chips in a microwave-safe dish until they are completely melted.
2. Place 12 peppermint candies in a zip-seal bag and use a rolling pin to crush them. 
3. Once cookie sandwiches are assembled, drizzle the melted chocolate across the tops of the coolies.  
4. Finally sprinkle the tops with crushed peppermint, allow the chocolate to set and enjoy.

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This story originally appeared in the December 2024 issue of 225 Magazine.