Prepare cake according to package instructions. Cool completely.
Cut cake into 1 inch squares; layer half of the cake in the bottom of an 8 inch trifle dish.
In a large chilled mixing bowl, combine heavy cream, sugar, and vanilla extract.
Using chilled beaters, beat on high speed until stiff peaks form.
Cut cream cheese into four pieces and add them to whipped cream.
Continue beating on high speed until cream cheese is fully incorporated.
Layer half of cream cheese mixture on top of gingerbread cake in trifle dish.
Top with one can cherry fruit filling.
Repeat layers, ending with cherry fruit filling on top.