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.