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"This is my idea of fall and winter all wrapped up in a pudding dish," Anne says. "I take basic custard and ratchet it up by adding pumpkin and maple syrup. Then to keep it super-sexy, I use challah, which is a rich, buttery, and slightly sweet bread. This isn't your ordinary, everyday bread pudding—this bread pudding is more like cake, and I like cake!"
Pro Swap: If you want to get really fancy, use cinnamon brioche or pound cake in place of the challah.
Check out more of Anne's favorite Thanksgiving recipes:
Frizzled Brussels Sprouts With Pancetta & Walnuts
Pumpkin Soup With Allspice Whipped Cream & Fried Leeks
[SKIP THIS STEP IF USING CANNED PUMPKIN PUREE] Preheat oven to 375˚F. Cut pumpkin into quarters, place on a baking sheet, and roast until fork-tender, about 1 hour. Remove from the oven and let cool (this can be done a day or two ahead). Once cool enough to handle, peel off the skin, remove the seeds, and puree flesh in a food processor.
To make the pudding, preheat oven temperature to 325˚F.
In a large bowl, combine pumpkin puree, heavy cream, brown sugar, eggs, maple syrup, cinnamon, nutmeg, allspice, and vanilla, and mix well.
Butter a 9-by-13-inch baking dish. Add bread, walnuts, and cranberries and toss to combine. Pour pumpkin mixture on top and let sit 30 minutes.
Bake until custard is set, 50 to 55 minutes.