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Stacked cookie sandwiches highlighting the contrast between dark chocolate layers and festive filling.

Stuffed Chocolate Peppermint Cookies Sandwich

These Stuffed Chocolate Peppermint Cookies Sandwich cookies feature rich chocolate cookies filled with creamy peppermint butter filling and finished with crushed candy canes for a festive holiday dessert.
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Course: Dessert
Cuisine: American
Keyword: Stuffed Chocolate Peppermint Cookies Sandwich
Prep Time: 20 minutes
Cook Time: 8 minutes
Total Time: 28 minutes
Servings: 18 cookies

Ingredients

For the Cookies

  • 1 3/4 c all-purpose flour
  • 1/2 c unsweetened cocoa powder preferably Dutch-process
  • 1/4 tsp salt
  • 1 c sugar
  • 3/4 c unsalted butter room temperature
  • 1 large egg

For the Filling

  • 2 c powdered sugar
  • 3/4 c unsalted butter room temperature
  • 3/4 tsp peppermint extract
  • 2 drops red food coloring or more as desired
  • 1/2 c crushed red-and-white striped candy canes or hard peppermint candies

Instructions

Prepare the dry ingredients.

  • In a large mixing bowl, whisk together the flour, cocoa powder, and salt. Set aside.

Cream the butter and sugar.

  • In the bowl of a stand mixer fitted with the paddle attachment, beat the sugar and butter together until well blended, about 3 minutes.

Add the egg.

  • Beat in the egg until fully incorporated.

Add the dry ingredients.

  • Add the flour mixture and mix on low speed until just combined.

Chill the dough.

  • Shape the dough into a disk, wrap it tightly in plastic wrap, and refrigerate for 1 hour.

Preheat the oven and prepare the baking sheets.

  • Preheat the oven to 350°F. Line 2 baking sheets with parchment paper.

Shape the cookies.

  • Roll a heaping teaspoon of dough into a smooth ball. Repeat with the remaining dough, placing the balls about 1 inch apart on the prepared baking sheets.

Flatten the cookies.

  • Using the bottom of a glass, gently flatten each dough ball.

Bake the cookies.

  • Bake for approximately 8 minutes, or until the cookies no longer appear wet and a slight indentation remains when the tops are lightly touched.

Cool the cookies.

  • Let the cookies cool on the baking sheets for 3 minutes, then transfer them to wire racks to cool completely.

Prepare the filling.

  • In the bowl of a stand mixer fitted with the paddle attachment, beat together the powdered sugar and butter until well blended. Add the peppermint extract and food coloring, then continue beating until the filling is smooth and evenly colored.

Assemble the cookie sandwiches.

  • Spread or pipe the filling evenly over the flat side of one cookie, extending it to the edges. Place a second cookie on top, flat side down, and press gently. Repeat with the remaining cookies.

Finish with crushed candy canes.

  • Place the crushed candy canes in a small shallow bowl. Roll the edges of the cookie sandwiches in the crushed candy canes.

Notes

To make these Stuffed Chocolate Peppermint Cookies Sandwich cookies gluten free, replace the all-purpose flour with a certified gluten-free 1:1 baking flour blend. Also confirm that the cocoa powder, powdered sugar, peppermint extract, food coloring, and candy canes are certified gluten free or free from hidden gluten-containing additives if needed for strict dietary requirements. If your gluten-free flour blend does not already contain xanthan gum, add it according to the package directions for the best cookie texture.