Place cookies in zip top bags. Use a rolling pin to roll over cookies and crush them. Place in a bowl and mix together.
Using a mixer, whisk together cream cheese, 8 oz. whipped topping, 1 C confectioner sugar. Spoon half of the mixture into a separate bowl. Fold pumpkin puree and pumpkin pie spice into remaining cream cheese mixture.
In small trifle dishes or pretty glasses, layer cookies, cream cheese mixture, pumpkin mixture. Repeat until dish is full. Top with leftover whipped topping and garnish with cookie crumbles.