Part 1: Prepare the Pudding and “Dirt”

1. Make the Pudding: In a large mixing bowl, combine the two packages of instant chocolate pudding mix with the 4 cups of cold milk. Whisk vigorously for about 2-3 minutes. You’ll feel the mixture start to thicken. Once it’s smooth and free of lumps, set it aside to firm up. You can place it in the refrigerator for about 5-10 minutes to expedite this process. The pudding should be thick enough to hold its shape.
2. Create the Oreo “Dirt”: While the pudding sets, it’s time to make the dirt. The easiest way is to place the entire package of Oreo cookies (cream filling and all!) into the bowl of a food processor. Pulse several times until the cookies are broken down into fine crumbs. If you want a more varied texture, leave some slightly larger pieces. If you don’t have a food processor, place the cookies in a large, sealed Ziploc bag, lay it flat, and crush the cookies using a rolling pin, meat mallet, or the bottom of a heavy pan. This method is also a fantastic and fun job for kids!
3. Lighten the Pudding: Retrieve your thickened pudding from the fridge. Gently fold in about three-quarters of the thawed whipped topping using a spatula. Mix until just combined, being careful not to overmix and deflate the whipped topping. This step lightens the pudding’s texture, making it creamier and less dense. Reserve the remaining whipped topping for another use or for a dollop on top if you wish.

Part 2: Craft the Cookie Tombstones

1. Prepare Your Workspace: Lay out your Milano cookies on a clean, dry surface like a cutting board or a sheet of parchment paper.
2. Write the Epitaphs: Using your black or red decorating gel or an edible ink marker, carefully write spooky messages on each cookie. “RIP” is a classic, but you can get creative with “Boo,” “Here Lies…”, or even draw small cracks or a cross.
3. Let Them Set: Set the decorated tombstones aside to allow the gel or ink to dry slightly so it doesn’t smudge during assembly.

Part 3: Assemble the Graveyard Pudding Cups

1. First Layer of Dirt: Spoon about 1-2 tablespoons of the crushed Oreo “dirt” into the bottom of each of your clear cups. This creates a solid base and looks great through the side of the cup.
2. Layer the Pudding: Spoon or pipe the lightened chocolate pudding mixture over the Oreo base, filling each cup about two-thirds full. Using a piping bag can help create clean, even layers, but a spoon works perfectly fine. Gently tap the cup on the counter to level the pudding.
3. Top with More Dirt: Generously sprinkle the remaining crushed Oreo cookies on top of the pudding layer in each cup. This is your graveyard’s topsoil. Be sure to cover the pudding completely.

Part 4: Decorate and Bring Your Scene to Life!

1. Plant the Tombstones: Take one of your decorated Milano cookie tombstones and gently press it into the pudding and Oreo dirt at a slight angle, towards the back of the cup. The pudding will act as an anchor to hold it in place.
2. Add the Worms: This is the fun part! Drape a few gummy worms over the edge of the cup, bury them halfway in the “dirt,” or have them crawling up the tombstone.
3. Final Spooky Touches: If using, strategically place your candy pumpkins near the tombstones. Sprinkle some bone-shaped candies or green-tinted coconut flakes (to look like moss) around the base of the headstone. A ghost Peep or marshmallow placed in the center can add another layer of spooky fun.
4. Chill Before Serving: For the best results, place the assembled Graveyard Pudding Cups in the refrigerator to chill for at least 30 minutes before serving. This allows the flavors to meld and ensures the pudding is fully set, keeping the tombstones standing tall.