Chocolate-Filled Cookies with Peppermint Frosting

Total Time

Prep: 35 min. + chilling Bake: 10 min. + cooling


about 2 dozen

Updated: Jun. 14, 2022
Baking is one of my favorite traditions around the holidays. These special cookies draw you in with candy-topped frosting and seal the deal with a chocolate center. —Deborah Puette, Lilburn, Georgia
Chocolate-Filled Cookies with Peppermint Frosting Recipe photo by Taste of Home
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  • 2/3 cup shortening
  • 1 cup sugar
  • 1 large egg
  • 1-3/4 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 2 milk chocolate candy bars (1.55 ounces each)
  • 2 cups confectioners' sugar
  • 2 tablespoons unsalted butter, melted
  • 1/4 teaspoon peppermint extract
  • 3 to 4 tablespoons evaporated milk
  • 24 miniature candy canes, crushed


  1. Cream shortening and sugar until light and fluffy. Beat in egg. In another bowl, whisk flour, baking powder, baking soda and salt; gradually beat into creamed mixture.
  2. Divide dough in half. Shape each into a disk; wrap in plastic. Refrigerate until firm enough to roll, about 30 minutes.
  3. Preheat oven to 350°. Break each candy bar into 12 pieces. On a lightly floured surface, roll each portion of dough to 1/8-in. thickness. Cut with a floured 2-in. square cookie cutter. Place half of squares 2 in. apart on ungreased baking sheets. Place a chocolate piece in the center of each square; cover with remaining squares, pressing edges to seal.
  4. Bake until edges are golden brown, 9-11 minutes. Remove from pans to wire racks to cool completely.
  5. For frosting, combine confectioners’ sugar, butter, extract and enough milk to reach a spreading consistency. Spread over cookies; sprinkle with candies.
  6. To make ahead: Dough can be made 2 days in advance. Wrap in plastic and place in a resealable bag. Refrigerate.

Can you freeze Chocolate-Filled Cookies with Peppermint Frosting?

Place wrapped dough in resealable plastic freezer bag and freeze. If necessary, let dough stand 15 minutes at room temperature before cutting. Prepare and bake cookies as directed. Iced cookies can be frozen up to 1 month.

Nutrition Facts

1 cookie: 209 calories, 8g fat (3g saturated fat), 12mg cholesterol, 94mg sodium, 33g carbohydrate (24g sugars, 0 fiber), 2g protein.

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