Roughly break up the gingersnaps and set aside.

In a large bowl, with hand mixer or stand mixer, beat the cream cheese until fluffy. Add the pudding and beat until combined and smooth.

In a medium (3- to 4-qt) trifle dish, arrange half of gingersnaps. Top with half of cream cheese mixture, smoothing in even layer. Press the gingerbread trees up against sides of trifle dish. Add 2-inch layer of raspberries and blueberries, reserving some for garnish.

Top with remaining cream cheese mixture. Add the jam, spreading in even layer. Top with remaining gingersnaps. Spread the whipped topping over gingersnaps.

Cover and refrigerate at least 3 hours and up to overnight. When ready to serve, decorate top with reserved berries and the gingerbread men.