In a stand mixer using the whisk attachment, add both ingredients to the bowl and whisk on medium/high speed until you get stiff peaks, roughly 4-5 minutes.
Note- stiff peaks are when you detach the whisk attachment and hold the whisk upside down, the whipped cream peak should stand straight up.
GINGERBREAD CHEESECAKE FILLING
In a stand mixer using the paddle attachment cream together the cream cheese and sugar on high speed for about 2-3 minutes. Scrape bowl and paddle once during this mixing.
Next, add the rest of the ingredients and mix on low speed for 30 seconds, then turn up to medium speed and mix until smooth and incorporated.
Last, fold in whipped cream.
GINGERBREAD TRIFLE
Add 2 bags of Gingerman cookies to a gallon-sized baggie and crush using a rolling pin or hands until cookies are crumbly but still have big chunks of cookie.
Pour a small amount of the crushed cookies on the bottom of each mason jar. This is your first layer in the trifle.
Add a good sized spoonful of the gingerbread cheesecake filling, enough to cover the cookies.
Add a spoonful of the whipped cream, enough to cover the cheesecake filling.
Then squeeze some of the caramel on top of the whipped cream.
Repeat layers until mason jar is full, ending with a whipped cream layer.