In a large mixing bowl, combine the heavy whipping cream, powdered sugar, pure vanilla extract, and peppermint extract. Using an electric mixer on medium speed, whip the mixture until stiff peaks form, which should take about 3 to 5 minutes. Be careful not to overwhip.
Take a 9x5 inch loaf pan and spread a generous thin layer of the whipped cream mixture evenly across the bottom.
Place a single layer of chocolate wafer cookies directly on top of the cream, ensuring that they cover the entire base.
Spread another layer of the whipped cream mixture over the cookies, smoothing it out to cover them completely. Lightly sprinkle some of the crushed peppermint candies over this layer.
Continue the process of layering: add more chocolate wafer cookies, followed by whipped cream, and then more crushed candy, until all ingredients are exhausted. Finish with a layer of whipped cream on top.
Cover the loaf pan tightly with plastic wrap and refrigerate for a minimum of 4 hours, but overnight is best.
Once the cake has chilled and set, gently remove it from the pan by inverting it onto a serving platter. If desired, add chocolate shavings and remaining crushed peppermint candies on top before slicing.
Notes
For an extra touch of holiday cheer, garnish each slice with a sprig of fresh mint and a sprinkle of powdered sugar.