Crush the Oreo cookies in a food processor until finely crumbed. Reserve 1 cup of the crumbs for garnish.
In a large mixing bowl, beat together the softened cream cheese and butter until smooth. Gradually add powdered sugar and mix until fully combined.
Fold in the whipped topping gently until well mixed.
In another bowl, whisk the instant chocolate pudding mix with the milk until thickened, about 2 minutes.
Fold the pudding mixture into the whipped topping mixture until well combined.
In a trifle dish or individual cups, layer crushed Oreos, the cream mixture, and repeat until ingredients are used up, finishing with a layer of crushed Oreos on top.
Cover with plastic wrap and refrigerate for at least 4 hours, or overnight.
Before serving, garnish with reserved Oreo crumbs and optional gummy worms for a fun touch.
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Notes
Store leftovers in the refrigerator for 3 to 5 days. Cover with plastic wrap or store in an airtight container.