In a large mixing bowl, combine the chocolate pudding mix with 2 cups of cold milk. Whisk vigorously for 2 minutes until smooth and slightly thickened. Allow to sit for 5 minutes to reach desired consistency.

Gently fold 1 cup of whipped cream into the pudding mixture using a spatula until smooth and fluffy.

Grab clear plastic cups or dessert glasses and spoon a generous amount of pudding mixture at the bottom of each cup for an even base.

Crush Oreos into fine crumbs and sprinkle a layer over the pudding in each cup. Use about 2 tablespoons per cup.

Repeat layering with another spoonful of chocolate pudding mixture over the crushed Oreos, followed by another layer of crushed Oreos.

Top each cup with a dollop of whipped cream for a fluffy finish.

Decorate each cup with candy pumpkins and optional gummy worms.

Refrigerate for at least 30 minutes before serving to allow flavors to meld.