Mix cream cheese, confectioners' sugar, and 1 teaspoon cinnamon together in a bowl; fold in 1 cup whipped topping. Spread cream cheese mixture into graham cracker crust and top with pecans.
Stir milk, pumpkin puree, pudding mix, 1 teaspoon cinnamon, and nutmeg together in a bowl until blended; fold in 1 1/2 cup whipped topping and spoon over cream cheese mixture layer.
Refrigerate pie for 1 hour. Top pie with remaining whipped topping and drizzle caramel topping over pie.
Caramel lovers can drizzle even more before layers, but beware, this is very rich.