Whip heavy cream, powdered sugar, and peppermint extract together until stiff peaks form.
Line a 9x5-inch loaf pan with plastic wrap, leaving overhang.
Spread a thin layer of whipped cream on the bottom of the pan.
Add a single layer of whole chocolate sandwich cookies, then spread a generous layer of whipped cream over them.
Repeat layering cookies and whipped cream until the pan is full, finishing with a whipped cream layer.
Scatter crushed candy canes and mini chocolate chips over the top.
Cover and freeze overnight. Lift out using plastic wrap and slice into 1-inch slices to serve.