Add milk to a large mixing bowl. Sprinkle in the chocolate pudding mix and whisk until smooth. Set in the fridge for 5 minutes until it has set.
While the pudding is setting, find a serving dish and set to the side.
In a large zip top bag, place the chocolate sandwich cookies. Crush with a rolling pin until the cookies are crumbs.
Start assembling the dessert. Add 1/4 of the pudding to the serving dish. Cover pudding with whipped cream, and sprinkle on a layer of cookie crumbs. Repeat until all pudding and cookies are gone (you should end with pudding-then add a final layer of crumbs.)
Poke gummy worms into the top of the dessert. Serve immediately.