Line a 9 x 5-inch loaf pan with plastic wrap. Set aside.

In the bowl of a stand mixer, fitted with a whisk attachment, whip the heavy cream until stiff peaks form. Alternately use an electric mixer or a hand mixer. Then add the peppermint and vanilla extracts and mix for a few seconds until combined.

Pour the sweetened condensed milk into the whipped cream and fold to combine.

Add the chopped cookies and peppermint bark, gently fold to combine. Reserve a few pieces to sprinkle on the top.

Pour the mixture into the prepared  loaf pan. Sprinkle the top with the chopped cookies, pieces of peppermint bark and candy cane pieces. Cover with plastic wrap and freeze for a minimum of 6 hours or overnight.