In a large mixing bowl, pour in 2 cups of chilled heavy cream and whip on medium-high speed for about 3–5 minutes until stiff peaks form.

In another bowl, combine 8 ounces of softened cream cheese and 1 cup of powdered sugar, blending on medium until smooth and creamy.

To the cream cheese mixture, add 1 teaspoon of vanilla extract and 1 teaspoon of peppermint extract, along with optional food coloring.

Gently fold in ½ cup of crushed peppermint candy into the cream cheese mixture.

Carefully fold the whipped cream into the cream cheese mixture using a spatula until fully incorporated.

Pour the peppermint filling into the pre-prepared chocolate Oreo crust and spread evenly.

Spread a layer of Cool Whip over the filling and sprinkle with crushed peppermint candy.

Cover with plastic wrap and chill in the refrigerator for at least 4 hours or overnight.