Preheat oven to 400°F and spray mini muffin pan with non-stick baking spray.
Using food processor, pulse together the gingersnap cookies, melted butter and sugar until it resembles wet sand.
Using hands, press about a tablespoon of the cookie crust mixture into each well of the mini muffin pan, pressing mixture down on the bottom and up the sides of each well.
Bake for 8 minutes, remove from the oven and lower the oven temperature to 350°F.
Using the backside of a small spoon, press each cookie crust cup down again and let cool for a few minutes.
Using stand mixer fitted with the flat beater attachment, mix together pumpkin, eggs, salt, pumpkin pie spice, sugar and evaporated milk until all combined.
Pour filling into each of the cookie cups and bake for 25 to 28 minutes, or until filling has set.
Using stand mixer fitted with the wire whip attachment, beat the cold heavy cream on medium-high speed (setting 4) until soft peaks form, after about 4 to 5 minutes. (Tip: Place beater bowl and wire whip, or whisk, attachment in the freezer 20 minutes before using.)
Add in sugar and pumpkin pie spice and beat again for another minute or two. Place whipped cream into a piping bag fitted with a star tip and top each pumpkin pie cookie cup with the pumpkin pie spice whipped cream. Drizzle on caramel, if desired. Serve immediately.