Dark Chocolate and Cranberry Challah Bread Pudding

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Growing up with both Christmas and Hanukkah in your home can inspire some wonderful crossovers, especially when it comes to the treats. We’ve partnered with Michelle Lopez, founder of Hummingbird High, who is turning the recipes she grew up with into some delicious holiday fusions.

In Jewish culture, challah is a fluffy, buttery, and braided brioche that is usually served as part of Friday night’s Shabbat meal; the meal begins with the lighting of the Shabbat candles and a quick blessing of two loaves of challah bread.

Growing up, my dad would sometimes come home on Friday nights with a couple honey-glazed loaves in honor of this tradition. And as much as we loved the challah, my family would always inevitably forget about the loaves of bread as we started tucking into our main dinner (because my mom’s cooking is that good).

Unfortunately, like any good brioche, sliced challah tends to go stale pretty quickly. By the second day, my siblings and I would turn up our noses anytime my mom tried to offer us any leftovers. So she started coming up with clever ways to “trick” us picky kids into finishing the loaves—think: challah grilled cheeses, French toasts, and more. My favorite trick of hers, however, was her impromptu challah bread pudding, made with whatever other leftover ingredients like spices and chocolate and fruit. My mom came up with some pretty good desserts.

Without further ado, I’ve followed my mom’s lead and made a bread pudding full of the leftover ingredients usually found during both Christmas and Hanukkah: challah, chocolate and cranberries. The combination is absolutely killer and pays an incredible homage to all the next-day challah bread puddings my mom whipped up during my childhood.

Dark Chocolate and Cranberry Challah Bread Pudding Recipe

(makes around 4 servings)


  • 10 ounces (around a 1-pound loaf) day-old challah, cut into 1-inch cubes
  • 2 large eggs, at room temperature
  • ¼ cup dark brown sugar, tightly packed
  • 1 teaspoon pure vanilla extract
  • ¼ teaspoon ground cinnamon
  • a pinch of kosher salt
  • 2 cups whole milk
  • ½ cup dark chocolate chunks or chips
  • ½ cup dried cranberries


Prepare four mini pie plates (or one 9-inch pie plate) by spraying with a generous amount of cooking spray. Divide 10 ounces cubed challah between the plates.

In a medium bowl, whisk together two large eggs, ¼ cup dark brown sugar, one teaspoon pure vanilla extract, ¼ teaspoon ground cinnamon and a pinch of kosher salt. Pour in two cups whole milk and continue whisking until the mixture is well combined and a uniform tan color. Pour the mixture over the bread cubes, dividing evenly between the pie plates. Let stand, pressing down on the bread cubes occasionally until they are evenly soaked, about 20 minutes.

While the bread is soaking, center a rack in the oven and preheat to 350 F.

Scatter ½ cup dark chocolate chunks and ½ cup dried cranberries over the soaked bread, dividing evenly between the pie plates. Use a spoon to gently toss the chocolate and cranberries into the mixtures.

Create a water bath by setting the pie plates in a large, shallow roasting pan and filling the pan with hot tap water until it comes halfway up the sides of the pie plate. If you can only fit two pie plates in the pan, no big deal — just bake two at a time.

Bake the water bath containing the pie plates in the preheated oven for 35 to 45 minutes, or until a skewer inserted into the center of the bread pudding comes out nearly clean. Once the bread pudding is ready, remove the pie plates from the water bath and allow to cool on a wire rack until warm and ready to eat. Enjoy immediately.

Want more recipes perfect for your Hanukkah celebration? Get the recipe for Gingerbread and Cookie Butter Rugelach and Sufganiyot, three ways.

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