Candy Cane Whoopie Pies Will Have You Shouting With Glee

Anna Painter
·2 min read

Yields: 32

Prep Time: 15 mins

Total Time: 1 hour

Ingredients

Cookies

  • 5 oz.

    bittersweet chocolate (70% cacao), finely chopped

  • 2 1/4 c.

    (270 g.) all-purpose flour

  • 2/3 c.

    (60 g.) unsweetened cocoa powder

  • 1 1/2 tsp.

    baking powder

  • 1/2 tsp.

    kosher salt

  • 1/2 tsp.

    baking soda

  • 1 c.

    (2 sticks) unsalted butter, softened

  • 3/4 c.

    (160 g.) packed light brown sugar

  • 3/4 c.

    (150 g.) granulated sugar

  • 2

    large eggs

  • 1/2 tsp.

    pure vanilla extract

Peppermint Frosting

  • 1 c.

    (2 sticks) unsalted butter

  • 4 c.

    (480 g.) confectioners' sugar, divided

  • 1 tbsp.

    water

  • 1 1/4 tsp.

    peppermint extract

  • 1/4 tsp.

    pure vanilla extract

  • Pinch of kosher salt

  • Red gel food coloring

  • 12

    mini candy canes, finely crushed

Directions

Cookies

  1. Arrange a rack in center of oven; preheat to 375°. In a small heatproof bowl, microwave chocolate in 30-second increments, stirring between each, until melted and smooth, about 1 minute total. Let cool.

  2. In a medium bowl, whisk flour, cocoa powder, baking powder, salt, and baking soda.

  3. In the large bowl of a stand mixer fitted with the paddle attachment, beat butter, brown sugar, and granulated sugar on medium speed until light and fluffy, 2 to 3 minutes. Add eggs and vanilla and beat until just combined. Fold in melted chocolate. With mixer on low speed, add dry ingredients and beat until just combined.

  4. Drop level tablespoons of cookie dough onto a parchment-lined baking sheet. (You should be able to fit 16 cookies on a sheet and have enough dough for 64 cookies.)

  5. Bake cookies until edges are set and centers look mostly done, about 6 minutes. Let cool on sheets 2 to 3 minutes. Transfer to a wire rack and let cool completely. Repeat with remaining dough.

Peppermint Frosting

  1. In the large bowl of stand mixer fitted with the paddle attachment, beat butter on medium speed until smooth. Add half of confectioners' sugar and beat until smooth. Add water, vanilla and peppermint extracts, and salt and beat until smooth.

  2. Add remaining confectioners' sugar and beat until smooth. (If frosting feels too thick, add 1 Tbsp. water.) Add 1 drop food coloring and beat to combine, adding more if needed until desired shade is reached.

  3. Turn half of cookies smooth side up. Spread or pipe frosting onto smooth sides, then close with remaining cookies.

  4. Place crushed candy canes on a plate. Roll cookie sandwiches so candy canes stick to frosting.

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