Ever since I first tried it, bread pudding has become one of my favorite homey desserts. Growing up I never knew it even existed. In my household, old bread was made into breadcrumbs not dessert (blame it on eastern European frugality). If you like French toast then there's no reason you wouldn't like bread pudding—they have similar preparations but with different cooking methods. I actually love it more than French toast, which is hard to say for someone who, as a kid, demanded his mom make French toast for breakfast every Saturday morning.
There's something special about the soft, moist cubes of bread in this dessert that makes me go weak in the knees. When I traveled through England during college, I couldn't help noticing bread and butter pudding (or spotted dick as they commonly call it) on almost every restaurant menu—and I always ordered it without restraint. It always came drenched in custard, which is the traditional way to serve it.
With this recipe I put a seasonal spin on the comforting bread pudding by adding puréed roasted butternut squash and replacing the classic raisins with dried cranberries. Once you dig into it, you'll be surprised how much it tastes like pumpkin pie—you might even consider making it every holiday from now on. Serve it for dessert with vanilla ice cream. It's also not bad for breakfast with some maple syrup.
Butternut Squash Bread Pudding with Dried Cranberries
2 tablespoons butter
1 16-ounce loaf Brioche, cut into 3/4-inch cubes
3/4 cup dried cranberries
2-1/2 cups whole milk
6 large eggs
1 cup roasted butternut squash purée
1 cup granulated sugar
1/4 cup rum
2 teaspoons pure vanilla extract
2 teaspoons ground cinnamon
Preheat oven to 350 degrees F. Spread the bread on a large rimmed baking sheet and toast for 10 minutes until dry and light brown.
Butter a 2-quart baking dish with 1 tablespoons butter. Add bread and cranberries.
In a large measuring cup or bowl, beat together milk, eggs, squash purée, and sugar. Stir in rum and vanilla. Pour over bread and toss to incorporate. Let soak in refrigerator for 1 to 2 hours.
Dust top with cinnamon. Dot the top with remaining butter. Tent with aluminum foil and bake for 30 minutes. Remove foil and continue to bake for another 20 minutes. Bread should be puffed and custard set. Let cool slightly before serving. Yield: 6 to 8 servings.