Prepare the Pudding: In a large mixing bowl, combine the milk and vanilla instant pudding. Whisk together until the mixture thickens. Set aside.

Crush the Oreos: Place the Oreos in a large ziplock bag. Using a rolling pin, crush the cookies into fine crumbs. Alternatively, you can use a food processor to achieve this. Set aside about 1/4 of the crushed Oreos for the top layer.

Make the Cream Cheese Mixture: In a separate mixing bowl, beat the softened butter and cream cheese together until smooth and creamy. Gradually add the powdered sugar, mixing until well combined.

Combine Pudding and Cream Cheese Mixtures: Fold the cream cheese mixture into the prepared pudding until thoroughly combined. Gently fold in the Cool Whip until the mixture is smooth and uniform.

Assemble the Trifle: In a trifle dish, start by adding a layer of the crushed Oreos at the bottom. Next, add a layer of the pudding mixture over the Oreos. Continue layering, alternating between the crushed Oreos and the pudding mixture, until you reach the top of the trifle dish. End with a layer of the reserved crushed Oreos.

Decorate: Decorate the top layer with gummy worms, placing them so they look like they're crawling out of the "dirt."

Chill and Serve: Refrigerate the dirt cake for at least 2 hours before serving to allow it to set. Serve chilled, scooping into individual bowls to reveal the layered "dirt" effect.