Put pudding packet contents into a glass bowl. Whisk in the milk. (To get milk very cold, put it in the freezer for 15 minutes).
In a clean bowl, using an electric beater or a whisk, beat together the cream with confectioners' sugar until soft peaks form.
Line each serving glass with a single layer of vanilla wafers and top with about 3 tablespoons of pudding mix, whipped cream, then a few slices of banana. Repeat creating 3 layers and finishing with a pudding layer. Allow to sit in refrigerator for at least 1 hour and up to overnight to set and soften the cookies.
Top each dessert with a generous dollop of whipped cream. Garnish with pumpkin pie spice, a vanilla wafer and slice of banana.