In a large bowl, crush your chocolate peppermint cookies (save some for topping), and in the same bowl whisk together the sweetened condensed milk, vanilla, and peppermint until combined.
Mix the heavy whipping cream on medium-high speed until stiff peaks are formed. I use a stand mixer on medium speed for 2-3 minutes. Slowly fold the whipped cream into the condensed milk mixture.
If desired, divide the ice cream mixture in half and add the red food coloring to half the mixture to turn it a wintery peppermint color. Leave the other half white.
Pour the mixture into the loaf pan, top with the extra cookie crumbles, and let this freeze overnight.
