Place bowl in the refrigerator to soft set, about 10 minutes.
Reserve about 1 1/2 cups of whipped topping to make ghosts later. Then take the pudding out and fold in the remaining whipped topping.
2 8 ounce whipped topping tubs
Place the bowl back in the refrigerator to chill for at least 15 minutes or up to 3 days.
Make Tombstones
Lay the Milano cookies or chocolate-covered graham crackers out on a baking sheet.
6 Milano cookies, 6 Chocolate-covered graham crackers
Write years or RIP on the cookies.
1 tube Writing gel
Crush Oreos
Add 6-8 Oreo cookies to a food processor and crush them into crumbs.
8 Oreo Cookies
Make Trees
Line a baking sheet with parchment paper.
Add 2-3 blocks of Almond Bark to a microwave-safe bowl.
1/2 cup Chocolate Almond Bark
Heat in the microwave for 1 minute, remove and stir. Continue cooking for 10-20 seconds until the chocolate is almost melted. Stir until completely melted and smooth.
Transfer chocolate to a plastic decorator bag or resealable bag and snip off a small amount of the end of the bag.
Create trees by piping melted chocolate onto parchment paper. Let set for 10-15 minutes until hard.
Assemble
Divide chocolate pudding filling into serving dishes or a 13x9 glass dish. **see notes
Sprinkle a layer of chocolate cookie crumbs over the pudding mixture.
Use the reserved cool whip to make "ghosts." Then add the decorations and gummy worms to the cups.
The number of servings for this dessert will depend on the serving dishes chosen. Use dessert cups, clear plastic party cups, or a 13 x 9-inch baking dish.
Make the components ahead of time but don't assemble the dirt cups until right before serving, or the cookies might become soggy.
If possible, use a food processor to make the Oreo dirt. Crushing them with a rolling pin won't result in fine crumbs.