Add the butter and sugar to the bowl of a stand mixer fitted with a paddle attachment. Beat together on high speed for 2 minutes or until creamy and fluffy.
Add in the eggs and beat for 15 seconds. Next, add in the milk, salt, and vanilla extract & peppermint extract. Beat together. Add in the flour and mix to combine completely.
Spoon the dough into a piping bag fitted with a large star tip. Hold the piping bag at a 90 degree angle above a parchment lined baking sheet. Pipe circle cookies onto the parchment in a counterclockwise motion, ensuring not to touch or overlap any of the cookies.
Use a clean finger to smooth the tail of the dough into the cookie. Place the baking sheet into the fridge to chill for at least 1 hour.
Once the cookies have chilled, preheat the oven to 350 F. Place the sheet of cookies into the oven to bake for 12 minutes.
Once baked, remove from the oven and place onto a cooling rack to cool completely.
Once cooled, dip each of the cookies halfway into the melted chocolate chips. Sprinkle with crushed candy cane pieces.
Let set at room temp or in the fridge until the chocolate has set.