A cross between pumpkin pie and French toast, this super-decadent caramel pumpkin bread pudding is an awesome addition to any Thanksgiving dessert spread. A rich base of eggy and buttery challah is key when it comes to making this comforting baked dessert. For the pumpkin, a blue skinned Jarrahdale pumpkin is awesome if you can find it, otherwise, butternut squash is a perfect substitution. Bonus: griddle up some slices of leftover bread pudding and drizzle with maple syrup for Black Friday breakfast.
Preheat the oven to 350 degrees F. In a large bowl, toss the challah with the 6 tablespoons melted butter. Spread in an even layer on a large baking sheet and bake until golden and crisp, about 20 minutes, stirring several times.2.
Meanwhile, in a large nonstick skillet, melt the remaining 2 tablespoons butter. Add the pumpkin and cook over moderate heat, stirring occasionally, until tender and browned, about 15 minutes. Sprinkle 3 tablespoons of the sugar on top and cook, stirring occasionally, until the sugar is glossy and caramelized, 5 to 6 minutes longer. Let cool slightly in the pan.3.
In the same large bowl, whisk the eggs with the milk, cream, cinnamon, nutmeg, cloves, salt, bourbon, and remaining 1 cup sugar. Add the challah and pumpkin and gently stir to combine. Let sit for 10 minutes to absorb the liquid. Pour the mixture into a buttered 9-inch by 13-inch baking dish and cover loosely with buttered foil.4.
Bake in the center of the oven for 20 minutes. Remove the foil, sprinkle with the pecans and bake until the top is golden and the center is set, 25 to 30 minutes longer. A toothpick inserted into the center should come out clean. Let cool slightly before serving with whipped cream.
MAKE AHEAD: The bread pudding can be prepared through step 3 and refrigerated overnight. Return to room temperature before baking.
Grace Parisi is a New York City-based food writer, cookbook author and food stylist. Her book, Get Saucy, was nominated for a James Beard award. Her latest book, Quick Pickles comes out in Spring 2016. Follow her on Instagram and Twitter.