Put the cranberries, whiskey, and 2 tablespoons water in a small bowl and soak until the cranberries are soft, about 1 hour.
Meanwhile, let the ice cream sit at room temperature until slightly softened, about 30 minutes. Transfer it to a bowl, then fold in the pumpkin spice. Cover and refreeze the ice cream.
Position a rack in the center of the oven and preheat the oven to 375 degrees F. Butter four 6-ounce ramekins and put them on a baking sheet.
Whisk together the eggs, heavy cream, milk, sugar, apples, cinnamon and salt in a medium bowl. Reserve 1 cup of bread cubes and add the remaining bread to the bowl with the egg mixture. Stir to combine and allow the bread to soak for at least 30 minutes. Add the cranberry mixture to the bread mixture and mix well, then spoon into the prepared ramekins. Toss the remaining bread cubes with the melted butter, then top the puddings evenly with the bread cubes. Bake the puddings until just set but still loose in the centers, about 20 minutes. Let the puddings rest at room temperature for 5 to 10 minutes before serving. Serve the puddings warm with a scoop of the spiced ice cream.
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