In a large mixing bowl, beat together softened cream cheese and butter until smooth.
Add cocoa powder, heavy cream, and chocolate syrup. Mix until well blended.
Slowly beat in powdered sugar until the dip is smooth and fluffy. Add a splash more cream if needed for consistency.
Spread the dip evenly into a shallow serving dish.
Sprinkle crushed Oreos over the top to resemble “dirt.”
Insert Milano cookies upright into the dip as gravestones. Use black icing to write “RIP” or spooky designs if desired.
Decorate with candy pumpkins around the tombstones.
Chill for 15–20 minutes before serving or enjoy right away.