Prepare the Oreo Soil: Place 10 Oreos in a zip-top bag and crush them using a rolling pin until they resemble coarse soil. Set aside.
In a large mixing bowl, add the softened cream cheese and unsalted butter. Using a hand mixer, whip them together until smooth and creamy.
To the cream cheese mixture, add the unsweetened cocoa powder and vanilla extract. Continue to whip until the ingredients are well combined.
Gradually add the powdered sugar to the mixture while continuing to whip. Ensure that the sugar is well incorporated and the mixture is smooth.
As needed, add the milk to the mixture, one tablespoon at a time, and whip until you reach a smooth and dip-like consistency.
Transfer the dip to a 1-quart dish, spreading it evenly to form the base of your graveyard.
Sprinkle the crushed Oreos over the dip to form the "soil" of the graveyard.
Prepare the Tombstones: On each Milano cookie, write phrases such as "RIP", "BOO", and "C U LATER" using the black icing or melted chocolate. Insert these "tombstones" into the dip at regular intervals.
Decorate the graveyard with candy corn, pumpkin candies, and sprinkles to add a festive and spooky touch.
Serve the dip with additional cookies or crackers for dipping. Enjoy your spooky Halloween graveyard chocolate cheesecake dip!