Ingredients

5 oz. bittersweet chocolate (70% cacao), finely chopped

2 1/4 cups (270 g) all-purpose flour

2/3 cup (60 g) unsweetened cocoa powder

1 1/2 tsp baking powder

1/2 tsp baking soda

1/2 tsp kosher salt

1 cup (2 sticks) unsalted butter, softened

3/4 cup (160 g) packed light brown sugar

3/4 cup (150 g) granulated sugar

2 large eggs

1/2 tsp pure vanilla extract

1 cup (2 sticks) unsalted butter

4 cups (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

Instructions

Step 1: Arrange a rack in the center of the oven and preheat to 375°F (190°C). In a small heatproof bowl, microwave the chopped bittersweet chocolate in 30-second increments, stirring between each, until melted and smooth. Let cool slightly.

Step 2: In a medium bowl, whisk together the flour, cocoa powder, baking powder, baking soda, and salt.

Step 3: In the large bowl of a stand mixer fitted with the paddle attachment, beat the softened butter, brown sugar, and granulated sugar on medium speed until light and fluffy, about 2 to 3 minutes. Add eggs and vanilla extract, beating until just combined. Mix in the melted chocolate.

Step 4: With the mixer on low speed, gradually add the dry ingredients and beat until just combined.

Step 5: Drop level tablespoons of dough onto parchment-lined baking sheets, spacing them apart. You should have enough dough for about 64 cookies, fitting 12 to 16 rounds per sheet.

Step 6: Bake the cookies for about 6 minutes, until edges are set and centers look mostly done. Let cool on the sheets for 2 to 3 minutes, then transfer to a wire rack to cool completely. Repeat with remaining dough.

Step 7: To make the peppermint frosting, beat the cup of butter in the stand mixer on medium speed until smooth. Add half of the confectioners’ sugar and beat until smooth.

Step 8: Add water, peppermint extract, vanilla extract, and a pinch of salt, and beat until smooth.

Step 9: Add the remaining confectioners’ sugar and beat again until smooth. If the frosting is too thick, add an extra tablespoon of water. Stir in 1 drop of red gel food coloring and beat until evenly colored. Add more drops if needed to reach the desired shade.

Step 10: Arrange half of the cooled cookies smooth side up. Spread or pipe frosting onto each, then top with the remaining cookies to form sandwiches.

Step 11: Place the crushed candy canes on a plate and gently roll each whoopie pie in them, pressing lightly so the candy sticks to the frosting.

Tips & Variations

For a stronger peppermint flavor, increase the peppermint extract slightly, but be cautious as it can overpower the frosting.

If you prefer a more subtle chocolate taste, use milk chocolate instead of bittersweet chocolate.

To make the frosting extra smooth, sift the confectioners’ sugar before adding it.

These whoopie pies can be decorated with colored sprinkles or crushed peppermint bark instead of candy canes for a different festive look.

FAQs

Can I make the cookie dough ahead of time?

Yes, the cookie dough can be made and refrigerated for up to 2 days before baking. Let it come to room temperature briefly before scooping and baking.

What can I use if I don’t have mini candy canes?

You can substitute regular candy canes crushed finely or use peppermint bark or crushed peppermint candies to get a similar festive crunch on the frosting.