Preheat your oven to 350°F (175°C) and line a cupcake tin with paper liners.
In a mixing bowl, whisk together flour, cocoa powder, sugar, baking soda, baking powder, and salt until well combined.
In another bowl, beat the softened butter until creamy. Add eggs one at a time, mixing after each addition. Stir in the vanilla extract.
Gradually add the dry ingredient mixture to the butter mixture, alternating with the buttermilk. Mix until just combined, being careful not to overmix.
Fold in the chocolate chips and crushed candy canes gently into the batter.
Divide the batter evenly among the cupcake liners, filling each about 2/3 full.
Bake in the preheated oven for 18-20 minutes or until a toothpick inserted into the center comes out clean.
Let the cupcakes cool in the tin for 5 minutes before transferring them to a wire rack to cool completely.
For the frosting, beat the powdered sugar, milk, and peppermint extract together until smooth and creamy. You may add more milk if needed for desired consistency.
Frost each cupcake generously with the peppermint frosting and sprinkle additional crushed candy canes on top for decoration.
Notes
Arrange the cupcakes on a festive platter and garnish with mini candy canes for a whimsical touch.