1. Two days before you plan to serve the pudding, prepare the bread: Place the yeast and water in a large mixing bowl and let stand until dissolved, 5 to 10 minutes. Meanwhile, whisk together the butter, pumpkin, honey, salt, eggs, and milk. Whisk this mixture into the yeast. Using a wooden spoon, gradually stir in enough flour to make a soft, pliable dough. Knead on a lightly floured surface until smooth and satiny, about 5 minutes.
2. Transfer the dough to a clean bowl, cover, and let rise in a warm, draft-free place until doubled, 1 to 1½ hours.
3. Butter a 9 × 5-inch loaf pan. Punch the dough down and transfer it to a lightly floured surface. Roll out into a 15 × 9-inch rectangle. Starting at one short side, roll the dough into a loaf and place in the prepared loaf pan. Cover and let rise again until doubled, about 1 hour.
4. Preheat the oven to 375° F.
5. Bake the pumpkin bread until crusty and brown on top, 45 to 50 minutes. Cool slightly, remove from the pan, and cool completely. Let the bread sit uncovered for at least a day before cutting into ½-inch cubes for the pudding. You will need 9 cups of loosely packed cubes for the pudding; save the remaining bread for another use.
6. Prepare the pears: Place the cider, liqueur, brown sugar, cinnamon, and nutmeg in a medium-size saucepan. Bring to a simmer over medium heat, stirring to dissolve the sugar. Add the sliced pears and cook 5 minutes. Remove the pears with a slotted spoon and set aside in a bowl. Simmer the remaining liquid until reduced to a thin syrup, about 30 minutes. Return the pears to the pan and cook a few minutes more, turning the pears to coat with the syrup. Set aside.
7. Preheat the oven to 350° F. Butter a 15 × 10-inch baking dish.
8. Place the 9 cups cubed pumpkin bread in the prepared baking dish.
9. Prepare the pumpkin custard: Scald the milk and cream together in a saucepan over medium heat. In a mixing bowl whisk together the eggs, pumpkin, sugar, cinnamon, and nutmeg until well blended. Whisk in the scalded milk and cream, then the liqueur. Pour the custard evenly over the bread in the baking dish.
10. Set the baking dish in a larger baking pan and add enough water to come 1 inch up the side of the dish. Bake the pudding 40 minutes. Spoon the pears and syrup over the top and bake until the custard is set, 20 to 25 minutes longer. Serve the pudding warm or at room temperature, drizzling each serving with Caramelized Amaretto Cream.