Prepare gingerbread cake mix and bake according to package directions (any size pan). Cool completely.
Place the pudding mix in a large bowl. Pour in the eggnog and whisk for about 2 minutes. Refrigerate pudding until the gingerbread cake is cool and you are ready to assemble the trifle.
In a large bowl, whip cream until stiff peaks are just about to form. Beat in sugar and vanilla until peaks form.
Crumble 1/2 of the gingerbread into the bottom of a trifle bowl or a large glass bowl. Spread 1/2 of the eggnog pudding over the gingerbread, then spread 1/2 of the whipped cream on top of the pudding. Repeat the layers with the remaining gingerbread, pudding, and whipped cream. Refrigerate 6 hours or overnight.
Sprinkle the top with the raspberries and cookie crumbs before serving. Makes around 10 cups of dessert so make sure your trifle bowl can hold that much.