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Chocolate Candy Cane Cookies

Adapted from: Bon Appétit Magazine, 12/2005

Course Dessert
Cuisine American
Keyword candy cane, chocolate, christmas baking, christmas cookies, cookie, frosting, holiday recipe
Prep Time 20 minutes
Cook Time 10 minutes
chill time, cool time 1 hour 30 minutes
Total Time 2 hours
Servings 10

Ingredients

Cookies

  • 1 3/4 cups all purpose flour
  • 1/2 cup unsweetened cocoa powder preferably Dutch-process
  • 1/4 teaspoon salt
  • 1 cup granulated sugar
  • 3/4 cup (12 tablespoons) unsalted butter, room temperature
  • 1 large egg
  • 2 tablespoons milk

Peppermint Frosting

  • 1 cup plus 2 tablespoons powdered sugar
  • 3/4 cup (12 tablespoons) unsalted butter, room temperature
  • 1/2 teaspoon peppermint extract
  • 1-2 drops red food coloring
  • 1/2 cup crushed red-and-white-striped candy canes about 4 ounces

Instructions

For cookies:

  1. Whisk flour, cocoa, and salt in medium bowl to blend. Using electric mixer, beat sugar and butter in large bowl until well blended. Beat in egg and 2 tablespoons milk. Add dry ingredients; mix just until blended.

  2. Refrigerate dough 1 hour or more.*

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

    Scoop out dough by level tablespoonfuls, then roll into smooth balls.

    Place dough on prepared baking sheets, spacing about 2 inches apart about 9-12 per baking sheet. Using bottom of small glass, slightly flatten each ball to about 1 1/2 inch round (edges will crack).

    Bake until cookies no longer look wet about 9-10 minutes (do not over bake or cookies will become dry). Let cool completely.

For filling:

  1. Using electric mixer, beat powdered sugar and butter in medium bowl until mixed well.

    Add peppermint extract and 1-2 drops food coloring depending on how much color you like in the filling. Beat until blended well.

    Spread 2 generous teaspoons filling evenly over flat side of 1 cookie and top with another cookie, flat side down. Repeat with remaining cookies and filling.

  2. Place crushed candy canes on plate. Roll edges of cookie sandwiches in crushed candies (candies will adhere to filling). Cookie sandwiches can be made ahead. Store in single layer in airtight container at room temperature up to 3 days or freeze up to 2 weeks.

  3. Makes about 10-12 small sandwich cookies

Recipe Notes

  • If refrigerating overnight, let dough sit on counter for 30 minutes before scooping out to bake. This will help the dough to be easier to scoop, but not allow it to thaw out completely. Preheat oven while the cookie dough is thawing a bit. 
  • If making ahead:  For best results, bake the cookies, let cool and freeze until ready to serve. Prepare the frosting, refrigerate up to a week. Crush the candy canes and store in an airtight container until ready to assemble cookies. When ready to assemble, let frosting sit at room temperature for an hour. Mix with a spoon.  Frost 1/2 of the cookies (flat side) with frosting, then place another cookie on top, again the bottom of cookie facing frosting. Roll in candy cane mixture when frosting is still soft. 
  • I have tried using pre-crushed peppermint pieces for this cookie, and found I like the look of crushed candy canes better than the pre-crushed peppermint.