Step 1: Make the Oreo Crust

1. In a food processor, pulse the Oreo cookies into fine crumbs. Alternatively, place the cookies in a sealed zip-top bag and crush them with a rolling pin.
2. In a medium mixing bowl, combine the crushed Oreos with the melted butter. Mix until the crumbs are evenly coated and resemble wet sand.
3. Press the mixture firmly into the bottom of a 9×13-inch baking dish to form an even crust. Use the bottom of a measuring cup or a flat spatula to pack it down tightly. Place the crust in the refrigerator to chill while you prepare the next layer.

Step 2: Prepare the Peppermint Cheesecake Layer

1. In a large mixing bowl, beat the softened cream cheese and powdered sugar together until smooth and creamy. Add the peppermint extract and mix until fully incorporated.
2. Gently fold in the whipped topping until the mixture is light and fluffy. Stir in the crushed peppermint candies or candy canes for added crunch and flavor.
3. Spread the peppermint cheesecake mixture evenly over the chilled Oreo crust, using a spatula to smooth the top. Return the dish to the refrigerator while you prepare the next layer.

Step 3: Make the Chocolate Pudding Layer

1. In a medium mixing bowl, whisk together the instant chocolate pudding mix and cold milk. Whisk for about 2 minutes, or until the pudding thickens.
2. Carefully spread the pudding over the peppermint cheesecake layer, ensuring it’s even and smooth. Return the dish to the refrigerator to set for at least 5 minutes.

Step 4: Add the Whipped Topping Layer

1. Spread the remaining whipped topping evenly over the chocolate pudding layer. Use a spatula or the back of a spoon to create smooth, even coverage.
2. Sprinkle crushed peppermint candies over the top for a festive garnish. Add mini chocolate chips, chocolate shavings, or crushed Oreos if desired.

Step 5: Chill and Serve

1. Cover the dessert with plastic wrap and refrigerate for at least 4 hours, or overnight, to allow the layers to set and the flavors to meld.
2. When ready to serve, slice into squares and use a spatula to carefully lift each piece out of the dish. Enjoy chilled.