Preheat oven to 350 degrees F. Line 32 muffin cups with paper bake cups. Place 1 gingersnap cookie in the bottom of each lined muffin cup; set aside.
In a very large mixing bowl, beat cream cheese and sugar until light. Remove 3/4 cup of the mixture; cover and chill. Beat pumpkin, the 1/4 cup whipping cream, the cinnamon, and allspice into the remaining mixture until smooth. Add eggs; beat until just combined. Spoon about 1/4 cup of the mixture into each cup.
Bake about 20 minutes or until centers appear set. Remove from muffin cups. Cool completely on a wire rack. Cover and chill for several hours or overnight.
Before serving, let the 3/4 cup chilled cream cheese mixture stand at room temperature for about 30 minutes. Stir in the remaining 1/4 cup whipping cream. Spread over the tops of the cheesecakes. Drizzle a little caramel topping on each cheesecake.
If desired, decorate additional gingersnap cookies with pumpkin faces using decorator icing.