In a large bowl, beat cream cheese and sugar with a mixer at medium speed until creamy. Add pumpkin and pumpkin pie spice, beating to combine. Fold in 1 container of whipped topping. Spoon pumpkin pie mixture into a piping bag fitted with a Wilton #2 tip.

Sprinkle 2 tablespoons crushed cookies into each of 6 mini trifle glasses. Pipe pumpkin pie mixture over crushed cookies, filling glasses 1/3 full. Spoon remaining container of whipped topping into a piping bag fitted with a star tip. Pipe a layer of whipped topping over pumpkin pie mixture. Sprinkle with crushed cookies, and pipe another layer of pumpkin pie mixture. Sprinkle crushed cookies in center, and pipe a border of whipped topping around edge of glasses. Refrigerate for at least 2 hours before serving.