While some family recipes for stuffing swear allegiance to cranberries, sausage, or oysters, here we’ve added chestnuts for a little flair but kept the rest of the dish familiar enough to be comforting.
1Heat the oven to 375°F and arrange a rack in the middle. Place the bread in a large mixing bowl; set aside. Coat a 3-quart baking dish with olive oil.
2Heat the 1 tablespoon of olive oil in a large frying pan over medium heat until shimmering. Add the pancetta and cook, stirring occasionally, until crisp and browned, about 10 minutes. Remove with a slotted spoon to a paper-towel-lined plate; set aside.
3Increase the heat to medium high, add the cinnamon to the pan drippings, and stir until fragrant, about 1 minute. Add the onion, fennel, salt, and pepper and cook, stirring occasionally, until the vegetables are just softened, about 10 minutes. Stir in the chestnuts and sage and cook until fragrant, about 30 seconds. Add the broth, stir to incorporate, and bring to a simmer.
4Pour the mixture over the bread, add the reserved pancetta, and stir well to evenly incorporate. Transfer the stuffing to the prepared baking dish and bake until it’s heated through and the bread is beginning to turn golden brown, about 30 minutes.