These festive Candy Cane Whoopie Pies are made for holiday sharing. Rich, chocolate-y cookies sandwich a silky peppermint frosting, then get rolled in crushed candy canes for a sweet, crunchy finish. Made with Gluten Free 1-to-1 Baking Flour, they’re a delicious addition to cookie swaps, holiday gatherings and gift boxes that everyone can enjoy.
These festive Candy Cane Whoopie Pies are made for holiday sharing. Rich, chocolate-y cookies sandwich a silky peppermint frosting, then get rolled in crushed candy canes for a sweet, crunchy finish. Made with Gluten Free 1-to-1 Baking Flour, they’re a delicious addition to cookie swaps, holiday gatherings and gift boxes that everyone can enjoy.
Preheat oven to 375°F. Line baking sheets with parchment paper. In a medium bowl, whisk together flour, cocoa powder, baking soda and salt.
In a large bowl, whisk together brown sugar, buttermilk, oil, egg and vanilla extract until well combined. Add the flour mixture and whisk just until combined. Add hot water and whisk until the batter is smooth.
Using a medium cookie scoop, or measuring about 1½ tablespoons of batter at a time, scoop batter onto prepared baking sheets, spacing cookies about 2 inches apart.
Bake for 8–10 minutes, or until the cookies spring back when lightly touched or a toothpick inserted into the center comes out clean.
Let cookies cool on the baking sheet for about 5 minutes, then transfer to a wire rack to cool completely.
Using an electric hand mixer or stand mixer fitted with the paddle attachment, beat butter, powdered sugar, vanilla extract, peppermint extract and salt until light and fluffy.
Add heavy cream and beat until smooth and silky. If the frosting is too thick to pipe, add additional heavy cream, 1 teaspoon at a time, until it reaches a smooth, pipeable consistency.
Pipe or scoop 2–3 tablespoons of frosting onto the flat side of half the cookies.
Top with remaining cookies, flat sides down, and gently press together until the frosting reaches the edges.
Place candy cane pieces in a shallow bowl. Roll the exposed frosting edges in the candy, gently pressing so the pieces adhere. Serve immediately or store in an airtight container.
Whoopie pie batter can be made 1 day in advance and stored in an airtight container in the refrigerator.
Peppermint frosting can be made up to 3 days in advance and stored in the refrigerator. Bring to room temperature before using, then re-whip until silky and smooth.
Dutch process or natural cocoa powder can be used. For the darkest color and more chocolatey flavor, use Dutch process cocoa powder.
Whoopie pies coated in candy cane pieces are best the day they’re assembled, but can be stored in an airtight container in the refrigerator for up to 2 days. Bring to room temperature before serving. The candy cane pieces may absorb moisture from the frosting and become soft or sticky over time.