In a large bowl, whisk together pudding mix and milk until combined. Let sit until thickened, about 3 minutes.
Make whipped cream: In the bowl of a stand mixer using the whisk attachment, or in a large bowl using a hand mixer, beat heavy cream with powdered sugar and vanilla until stiff peaks form.
Fold whipped cream and about ⅓ of crushed Oreos into chocolate pudding.
Divide between serving cups (or transfer to a trifle dish), then garnish each serving with more crushed Oreos and gummy worms.
Recipe by 5* trending recipes with videos at https://food.theffeed.com/2022/09/24/dirt-pudding/