In a large mixing bowl, whip the heavy cream until stiff peaks form. Set aside gently.
In another bowl, combine softened cream cheese and powdered sugar. Mix until smooth and creamy.
Incorporate the vanilla extract and peppermint extract into the cream cheese mixture. Add red food coloring if using.
Gently fold the whipped cream into the cream cheese mixture using a spatula.
Pour the creamy filling into the prepared chocolate cookie crust. Spread it out evenly.
Spread a layer of Cool Whip on top and sprinkle crushed peppermint over it.
Chill the pie in the refrigerator for at least 1-2 hours, or ideally overnight.
Notes
Garnish with extra crushed peppermint just before serving. Let cream cheese sit out for smoother filling. Aim to chill the pie for at least 4 hours for the best texture.