Pulverize the Oreos.
In a food processor, pulverize one package of Oreos for about 1 minute until they are a sandy texture. Combine with soft cream cheese.
In a large bowl, use a rubber spatula to combine the pulverized Oreos with the cream cheese until well mixed and a dough-like consistency. If the cream cheese got too soft, and it isn’t a dough consistency anymore, you can pop it in the fridge for 10 minutes until it's firm enough to hold a shape.
Roll into balls. Roll the Oreo cream cheese mix into 2-inch smooth balls and place them on a flat nonstick surface like a cutting board or parchment paper.
Optional - Create the pumpkin grooves.
Once all the balls are rolled, use a toothpick to press vertical lines into the balls representing the grooves on the pumpkins. Place them in the fridge to chill for at least 1 hour.
Coat in candy melts.
In a small bowl, melt the orange candy melts according to the package instructions. Once melted, remove the Oreo balls from the fridge. Use a fork to transfer one of the balls into the candy melts, rolling it around so it becomes evenly coated. Allow the excess to drip off and return it to the non-stick surface.
Add the stem and leaf.
Immediately place a half pretzel stick in the top to form a pumpkin stem and a half M&M (chocolate flat side down) next to the stem to make a pumpkin leaf. Repeat for all the pumpkins, and set aside in your fridge to set and harden while you make the pudding cups.
Pulverize another package of Oreos.
In a food processor, pulverize the second package of Oreos until they’re the texture of sand and place them in a bowl. Add a few spoonfuls to each cup and add a worm on top. Have your pudding handy and add a few spoonfuls on top of each gummy worm.
Layer the Oreos and pudding.
In 5.5-6 ounce clear snack cups, alternate layers of the pudding with Oreo crumbles, incorporating some of the gummy worms into each layer until the cups are filled. Top with Oreo crumbles. Add the pumpkins and sprinkles and serve.
Continue to layer the Oreo crumbles and pudding in clear snack cups, adding gummy worms into most layers until the cups are filled. Top with Oreo crumbles.
Add your pumpkin Oreo balls to the top. Sprinkled with green sprinkles, and serve chilled.