Prepare a 9-inch spring form by double-wrapping the bottom with foil. Preheat oven to 315F.
Prepare the graham cracker crust first. Place cookies into a food processor and pulse until broken down into fine crumbs. Pour in melted butter and pulse again until cookie crumbs are coated. Transfer cookie crumbs into prepared spring form pan and press firmly into the bottom of the pan to form a firm crust; set aside.
Prepare the cheesecake filling. Place softened cream cheese into mixer bowl and beat on medium-high speed for about 5 minutes until creamy and no clumps remain. Scrap down sides of bowl often to get all the cheese mixed together. Next, add the sour cream, sugar and vanilla. Mix again for a few minutes. Then add the 4 egg and mix again.
Divide the batter evenly between two bowls. Into one bowl, add the pumpkin puree, spices and maple syrup extract. Fold in the ingredients gently until creamy and smooth. Into the second bowl, add the dulce de leche, or a similar caramel. Use a whisk to mix the caramel and cheesecake filling together.
Pour the caramel filling over the crust first. Gently spoon the pumpkin filling over the top to create 2 distinct layers.
Transfer the cheesecake into a deep oven-roasting pan or baking dish. Fill the pan with water – this is easier once the pan is on the oven rack. Bake the cheesecake for about 2 hours, or until the edges are completely set. Turn oven off, crack open oven door and allow the cheesecake to sit for about 30 minutes. Then remove the cheesecake from the oven and cool at room temperature for a few hours before refrigerating overnight.
Prepare the whipped cream before serving. Combine chilled heavy cream, sugar, vanilla and cinnamon and whisk together until stiff peaks form. Transfer into a pastry bag for garnishing the cheesecake.