Preheat the oven to 350°F.
Add room temperature butter to a mixing bowl with the brown and white sugar. Beat with an electric hand mixer until everything is creamed together nicely.
Add in baking soda, baking powder, espresso powder, salt and cocoa powder. Mix until well blended.
Then, beat in eggs and peppermint extract.
Lastly, alternate adding the flour and milk in increments, beating the batter between each one (about 3-4 items alternating, adding ½ cup of flour at a time).
Fold in dark chocolate chips using a rubber spatula.
Pour the bread batter into a parchment lined or heavily greased loaf pan.
Bake your Chocolate Peppermint Loaf for 50-60 minutes or until a toothpick comes out clean from the center - this is important! The dark color of this bread, it may look done but will still be gooey in the center, so be patient.
While the bread bakes, make the frosting. In a medium mixing bowl, beat all the ingredients besides the crushed candy canes together until the powder sugar is completely mixed.
Let the bread cool completely, frost with the icing, and top with crushed candy cane pieces.
Slice and enjoy! I like to serve with a cold glass of milk.