In a large bowl, using a hand mixer beat the heavy cream, when it becomes frothy, slowly add the sugar while continuing to mix. Beat the cream to soft peaks.
Add the pudding mix to the milk, and whisk to combine. (Do this in the measuring cup.)
In another large bowl, beat the cream cheese with the sweetened condensed milk until smooth. (There is no need to clean your mixer whisks.) Add the pudding mixture, and again beat until smooth. Using a rubber spatula, gently fold in half of the whipped cream.
In a trifle bowl, or other tall clear serving dish, add half of the cubed pumpkin bread. Top with one third of the pudding mixture, then half of the apples and half of the pecans. Repeat layers, reserving a couple tablespoons of the pecans to garnish. Top the whole dish with the remaining whipped cream and pecans.
Serve immediately or cover with plastic wrap and refrigerate until ready to serve. Best within 2 days.
Recipe by Work. Cook. Eat. at https://www.workcookeat.com/thanksgiving-trifle/