Step 1: In a large mixing bowl, beat the softened cream cheese with an electric mixer until it is completely smooth and creamy, about 2-3 minutes.
Step 2: Gradually add the powdered sugar, vanilla extract, peppermint flavoring, and red food color to the cream cheese mixture. Beat on medium speed until well combined and fluffy, scraping down the sides of the bowl as needed.
Step 3: Gently fold in 1/2 cup of crushed peppermint candy into the cream cheese mixture using a spatula.
Step 4: In a separate, chilled bowl, whip the heavy whipping cream on high speed until stiff peaks form.
Step 5: Carefully fold the whipped cream into the peppermint cream cheese mixture until no streaks of white cream remain, being careful not to deflate the mixture.
Step 6: Pour the prepared filling into the Oreo pie crust and spread it evenly with a spatula or the back of a spoon.
Step 7: Place the pie in the refrigerator and chill for at least 4 hours, or ideally overnight, to allow it to set completely.
Step 8: Before serving, spread the thawed whipped topping evenly over the set pie. Sprinkle generously with additional crushed peppermint candy for garnish. Slice and serve immediately.