Chewy Chocolate Peppermint Holiday Sandwich Cookies

Chewy Chocolate Peppermint Holiday Sandwich Cookies

There are of course a million holiday cookie options out there, but these chewy chocolate peppermint holiday sandwich cookies are easy and next level. I personally like to use Steen’s cane syrup (this is not sponsored, I just love the stuff) in place of molasses, but you can totally use either! Cane syrup isn’t always easy to find but it can really bring your baking to the next level.

What you’ll need:

For the cookies:

  • All purpose flour
  • Dark cocoa powder
  • Baking soda
  • Salt
  • Butter, softened
  • Brown sugar
  • Granulated sugar
  • Egg
  • Cane syrup OR molasses
  • Vanilla extract
  • Raw (demerera) sugar for rolling

And for the buttercream filling:

  • Butter
  • Powdered sugar
  • Peppermint extract
  • Heavy cream
  • Crushed peppermint or candy canes

Instructions for Chewy Chocolate Peppermint Holiday Sandwich Cookies

These chewy chocolate peppermint holiday sandwich cookies are pretty straightforward!

Prepare your ingredients

Measure out the dry ingredients and set aside. Softened your butter and measure out the sugars and cane syrup or molasses. Get the egg out of the fridge.

Preheat the oven

Preheat the oven to 325 degrees F and line two baking sheets with parchment paper.

Make the dough

In a stand mixer with the paddle attachment or with an electric handheld mixer, beat the sugars and butter together until light and fluffy. Scrape the sides and add in the cane syrup or molasses. Add in the egg and vanilla and scrape the sides again.

Add in the dry ingredients a little at a time, mixing well but try not to overmix the dough. As soon as it comes together, stop the mixer.

Scoop out the cookies using a 1 1/2 tbsp cookie scoop, roll them in a ball, and roll them in the raw sugar. This gives the nice outer crunch to them! You should get about 24 cookies. Place 12 evenly spread out on each sheet.

Bake the cookies

No chilling required! Place the sheets right into the oven and bake for 11-12 minutes. They’ll still be slightly puffy and will deflate as they cool. Be sure not to overbake them as they’ll lose the chewy factor.

Allow to fully cool before you make the buttercream.

Buttercream Filling Time

Using the stand mixer with paddle attachment or electric handheld mixer again, beat all ingredients for the buttercream together, starting on low and working your way up to high. Scrape the sides as necessary. Beat it on high for about 45 seconds to a minute to really get it nice and airy.

Transfer to a piping bag or a ziplock bag with a hole cut from a corner for ease of piping onto the cookies. Pipe onto one side of a cookie and top with a second cookie. Roll them in the crushed peppermints.

Enjoy!

Other great cookie recipes:

Chewy Chocolate Peppermint Holiday Sandwich Cookies

Course: Dessert
Cuisine: Cookies, Dessert
Servings: 12 cookies

Ingredients

Cookies:

  • 2 cup all purpose flour
  • 1/3 cup special dark cocoa powder or sub normal cocoa powder
  • 1 tsp kosher salt
  • 1 tsp baking soda
  • 3/4 cup butter softened
  • 1/2 cup brown sugar
  • 1/2 cup granulated sugar
  • 1 egg
  • 1/4 cup cane syrup OR molasses
  • 1 tsp vanilla extract
  • raw sugar for rolling

Peppermint Buttercream

  • 1 stick butter, soft (1/2 cup)
  • 1 3/4 cup powdered sugar
  • 2 drops peppermint extract just a little!
  • 1 tbsp heavy cream
  • Crushed peppermint for rolling

Instructions

Make the cookies:

  • Preheat oven to 325 degrees F and line two baking sheets with parchment paper.
  • Combine the dry ingredients and set aside.
  • Cream the butter and sugars together until fluffy with a stand mixer with paddle attachment or an electric handheld mixer.
  • Scrape the sides and add in the cane syrup or molasses. Beat again.
  • Add in the egg and vanilla and beat again. Scrape the sides.
  • Add in the dry ingredients a little at a time, being sure not to overmix the dough once it comes together.
  • Scoop the cookies using a 1 1/2 tbsp cookie scoop. Roll them into balls and roll in the raw sugar. Spread 12 evenly across each baking sheet.
  • Bake for 11-12 minutes, careful not to overbake or they'll lose their chewiness. Remove from oven and allow to cool completely. They'll deflate as they cool!

Make the buttercream:

  • Beat all ingredients for buttercream together on low and work your way up to high, scraping the sides of the bowl as necessary. Beat on high for about a minute to ensure light and fluffy texture.
  • Scoop the buttercream into a piping bag or a ziplock with a hole cut in the corner. Pipe the buttercream onto the bottom of a cookie and top with a second cookie.
  • Roll the sides in crushed peppermint.
  • Enjoy!
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