1. Place the Gingerbread Oreos in the food processor and pulse a few times, until you have fine crumbs for the crust.
2. Divide the crumbs between six parfait cups or small canning jars. Gently press the crumbs into the bottom of each serving dish.
3. In the bowl of a stand mixer fitted with the paddle attachment, or in a medium bowl with a hand mixer, combine cream cheese, confectioners' sugar, pumpkin pie spice, vanilla extract, and Gingerbread Pudding. Mix on low speed until all ingredients are well combined.
4. Using a rubber spatula, fold in Cool Whip until completely incorporated.
5. Spoon or pipe cheesecake filling into each serving cup.
6. If desired, pipe additional Cool Whip onto each mini cheesecake, then place one Wilton Gingerbread Man on top of the whipped cream for a festive look.
7. Store in refrigerator until ready to serve.