In a large mixing bowl or the bowl of a stand mixer, combine cream and sugar. Beat until stiff peaks form and set aside.
To make the crust, place cookies and butter in a food processor, pulse until finely ground. Press into a 9-inch pie plate and bake at 350°F for 10 minutes. Set aside to cool.
Combine pudding mix, pumpkin, milk and cinnamon in large bowl until well combined. Fold in half of the whipped cream and pour into your prepared crust.
Top pie with the remaining whipped cream, drizzle with caramel sauce and sprinkle the pecans on top.
Refrigerate for at least 1 hour (or overnight) before serving.
* You can also try make this in a springform pan, but I would recommend popping the cake in the freezer before unmolding/serving -- just be sure not to let it warm up too much or it might start to collapse!