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Chocolate-Peppermint Sandwich Cookies

Chocolate-Peppermint Sandwich Cookies
3 votes, 4.00 avg. rating (79% score)
Chocolate-Peppermint Sandwich CookiesPhoto/Art by Michael Piazza

Total Time: 1 hour, 20 minutes

Hands On Time: 35 minutes

Yield: about 3 dozen cookies

These delicious Chocolate-Peppermint Sandwich Cookies are a nod to the current craze for “gourmetified” junk-food classics. In fine bakeries around New England, we now see tongue-in-cheek artisanal interpretations of Oreos, whoopie pies, and Pop-Tarts. Here, we took the Oreo meme a step further, adding crushed candy canes for a little holiday pizzazz.

Find more recipes for "Cookies Through the Decades."

For the cookies:

Ingredients:

  • 1-1/2 sticks unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg, at room temperature
  • 1-1/2 cups all-purpose flour
  • 1 teaspoon vanilla extract
  • 2/3 cup Dutch-process cocoa powder
  • 1/2 teaspoon table salt

Instructions:

Line 2 baking sheets with parchment paper and set aside. Using a standing or hand-held mixer, cream the butter and sugar in a large bowl until fluffy, about 2 minutes.

Beat in the egg and vanilla. Sift the flour, cocoa, and salt into the bowl, and beat at low speed until the dough comes together, about 1 minute. Turn out onto a counter dusted with confectioners’ sugar and knead 2 or 3 times. Flatten into 2 disks, wrap in plastic, and chill at least 30 minutes, or up to overnight.

Meanwhile, make the filling: In a clean bowl, cream together the butter, shortening, confectioners’ sugar, vanilla, and salt. Gather, press into a disk, wrap in plastic, and refrigerate while you prepare the cookies.

Preheat your oven to 350° and position 2 racks in the middle with space in between. Dust the counter with more confectioners’ sugar, and roll out the first portion of dough to a 1/8-inch thickness.

Use a 2-inch round biscuit cutter or cookie cutter to cut the dough into circles, gathering and rerolling as needed; then transfer to the baking sheets, about an inch apart. Repeat with the remaining dough. Transfer to the oven and bake until firm and fragrant, rotating the pans halfway through, 10 to 12 minutes. Remove the cookies from the oven and let cool on trays.

For the filling:

Ingredients:

  • 1/2  stick (4 tablespoons) unsalted butter, softened
  • 1/4 cup vegetable shortening
  • 2 cups confectioners’ sugar, plus more for work surface
  • 1-1/2 teaspoons vanilla extract
  • 1/4 teaspoon table salt
  • 1 cup finely crushed candy canes or peppermint candies

Instructions:

While the cookies are baking and cooling, dust your counter with additional confectioners’ sugar and roll the filling out until it’s about 1/8 inch thick. Use the same cutter to cut out frosting rounds the same size as the cookies. Refrigerate the disks as needed to keep them firm.

When the cookies are cool, sandwich a piece of frosting between two cookies, and press gently; then roll in the crushed candy.  

Updated Monday, November 4th, 2013

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