In a medium bowl, whisk together flour, cocoa powder, baking soda and salt until combined. Set aside.
In the bowl of a stand mixer, beat butter for 1 minute on medium speed until smooth and creamy. Add sugars and beat on medium high until fluffy. Beat in egg, vanilla and peppermint extract until combined. Scrape down the sides of the bowl as needed.
Slowly add the dry ingredients to the wet ingredients, beating slowly until combined. Add milk, beating until combined well.
Cover with plastic wrap and chill the dough for 3 hours. You can also chill the dough overnight if you want!
Preheat oven to 350 degrees. Line two large baking sheets with parchment paper or silicone baking mats.
Form approximately 2 Tbsp of dough at a time into balls. Place on baking sheets.
Bake for 10 minutes until baked on the edges but still soft in the center. Let cool for 5 minutes on the cookie sheets. Transfer to cooling rack to cool completely.
Once the cookies are cool, melt the white chocolate chips in the microwave in 30 second increments, stirring in between each, until melted.
Dip the cookies halfway into the melted white chocolate. Place on parchment paper and sprinkle the white chocolate with crushed candy canes. Let rest in a cool place until set, approximately 15 to 20 minutes.