1 package (14.3 oz) chocolate sandwich cookies (such as Oreos)
12–18 candy pumpkins (mellowcreme pumpkins)
1 tube of green decorating icing
6 clear plastic cups (8 or 10 oz size)
Instructions
Prepare the Cookie Crumbs: Place the chocolate sandwich cookies into a large resealable plastic bag. Use a rolling pin or a heavy spoon to crush the cookies until they resemble fine dirt or soil. You can leave a few larger chunks for texture if desired. Set these aside in a small bowl.
Mix the Pudding Base: In a large mixing bowl, whisk together the instant chocolate pudding mix and the cold milk. Continue whisking for about 2 minutes until the mixture begins to thicken. Let it sit for another 5 minutes to fully set.
Fold in the Whipped Topping: Gently fold the thawed whipped topping into the prepared chocolate pudding. Use a spatula to combine them until the mixture is light, fluffy, and uniform in color. This creates a mousse-like consistency that is much lighter than plain pudding.
Layer the Cups: Begin the assembly by placing a spoonful of the crushed cookie “dirt” at the bottom of each clear plastic cup. Follow this with a generous layer of the pudding mixture. Continue alternating layers of cookies and pudding until the cups are nearly full, ending with a thick layer of cookie crumbs on top.
Decorate the Pumpkin Patch: Place two or three candy pumpkins on top of the cookie crumbs in each cup. Using the green decorating icing, pipe small “vines” and “leaves” around the pumpkins to make them look like they are growing in a real patch. Serve immediately or chill until ready to eat.