In a small saucepan, heat apple cider and cranberries over medium heat, Bring to a boil and continue boiling until the cranberries have plumped up and almost all of the liquid has evaporated, about 4-5 minutes. In the meantime, preheat oven to 350-degrees F.
Remove cranberries from heat, transferring to a bowl and put in the refrigerator to cool about 15 minutes. With a pointed steak knife, cut off the tops of Asian pears, about 2-inches down from the stem. Carefully dig out the center of each, taking out core, but make sure you leave as much of the pear 'wall' as possible. Place, cut side up, into the muffin tin; set aside. Equally divide the Indian Pudding among the pear cavities, pressing as firmly as possible, level with the tops. You may have some pudding left over, but you can enjoy that while this dessert is baking.
In a bowl, combine both sugars, butter, cinnamon, bacon and cooled cranberries, along with any juice. Drizzle desired amount of maple syrup into the hole of each pear. Evenly divide the sugar mixture among the pears and bake 30-35 minutes, or until they are soft but still a little firm to the touch. Remove to cool slightly before serving.