Crumble cookies and graham crackers using a blender, food processor or plastic bag and rolling pin, and set aside.
In a large mixing bowl, make instant vanilla pudding according to box directions. Then, fold in whipped topping.
Using small clear cups, layer in cookie crumbs and a few spoonfuls of the pudding mixture. Repeat until you reach the top of the cup. Make sure to end with the cookie crumble.
Decorate with gummy bears, candy and mini umbrellas.
Chill in the refrigerator for at least 30 minutes before serving.