Crush the entire package of cookies in a large zipper baggie using a rolling pin or the smooth edge of a meat grinder.
Mix together pudding and cream cheese in a medium bowl with a hand mixer until smooth. Add pumpkin, sugar, and pumpkin pie spice; mix until blended.
Spoon a layer of crushed cookies into each of 12–15 small serving dishes, saving a few spoonfuls for topping. Top cookie layer with pumpkin mixture; divide evenly between the dishes.
Chill if desired.
Top each with a sprinkling of crushed cookies, a serving of whipped topping, and a dash of pumpkin pie spice just before serving.
Notes
Make sure the cream cheese is really softened; otherwise, it will be chunky. You can use the full package of cream cheese.
Ready to roll pie crusts, cream cheese, sugar, vanilla extract, egg, pumpkin puree, evaporated milk, light brown sugar, eggs, pumpkin pie spice, salt, water