Place the cookies and bourbon or bourbon vanilla into the bowl of a food processor and pulse until the cookies are broken down into fine crumbs.

Spoon about 3-4 tablespoons of the cookie crumbs into the bottoms of 12 dessert glasses and set aside.

Place the mascarpone cheese, pumpkin puree, whipping cream, sugar, vanilla, and pumpkin pie spice into a large mixing bowl. Mix on low speed to combine to combine the ingredients, and then increase to high speed to whip the ingredients until soft peaks form.

Place the pumpkin cream mixture into a large freezer bag, and cut the tip off of one corner. Pipe about ½ cup of the pumpkin cream over the cookie crumbs in each dessert dish. Sprinkle any remaining cookie crumbs over the top to garnish.

Refrigerate for at least 2 hours, or overnight.