In a large bowl, combine milk and pudding mix. Beat with a whisk until well blended.
Let stand 5 minutes.
Add whipped topping and half of the crushed cookies and fold in.
Place 1 Tablespoon crushed cookies into each cup. Fill cups 3/4 full with pudding mixture. Top with remaining crushed cookies. Refrigerate 1 hour. Decorate before serving.
Suggested Decorations: small paper umbrellas, gummy worms, gummy sharks, candy stars, chopped peanuts.