Total Calories: 114
Place cookies in a plastic sandwich bag and crush with a rolling pin (you will need 1 cup crumbs) set aside.
In a chilled small mixer bowl, beat milk, pudding mix, whipped topping mix and vanilla at low speed for 2 minutes. Increase speed to medium-high and beat 2 to 3 minutes longer or until thick and very fluffy. You should have about 4 cups of the mixture. At low speed, fold in the chips.
To assemble, spoon 1 tablespoon of the crumbs into each cup. Carefully spoon 1/2 cup of the pudding mixture into each cup. Sprinkle with 1 tablespoon of the crumbs. Loosely cover and chill at least 30 minutes or overnight.
Before serving, place a gummy worm in each cup on top of the "dirt" or have it climbing out of the cup.
Note: For easy handling and transporting, place filled cups in a 13 x 9 x 2-inch baking pan before loosely covering. Carry the cups in the baking pan.