Beat the softened cream cheese in a large bowl until smooth. Add the instant chocolate pudding mix and milk, then beat until the mixture thickens and combines evenly.

Fold in the whipped topping until no streaks remain. Stir in 1 cup of the crushed Oreo cookies to create the dirt texture.

Spread the dip across the center of a serving board. Sprinkle the remaining crushed Oreo cookies over the top for extra crunch and color.

Press the gummy worms into the dip so they look like they are coming out of the ground. Stand the Milano cookies upright along one edge of the dip to act as tombstones.

Arrange the crackers, pretzel sticks, and carrot sticks around the dip on the board for easy dipping.