Making a sweet & savory butternut squash bread pudding

Mass Appeal

(Mass Appeal) – We’re spending some time in the kitchen today with our good friend Jessie-Sierra Ross, creator of the blog Straight To The Hips, Baby making a Butternut Squash bread pudding.

Using a cinnamon & brown sugar roasted butternut squash custard base, we’ll layer cubes of challah bread with juicy sweet apples, dried cherries, and savory rosemary, to create the perfect Thanksgiving or Christmas dinner side dish! Even better? You can make this rich bread pudding side dish ahead of time and save yourself some extra time!

Makes 6-8 servings


1 small to medium butternut squash
1/2 stick of salted butter, divided into 4 tablespoon cubes
1 tablespoon light brown sugar
1/4 teaspoon ground cinnamon
1/4 teaspoon + 1/8 teaspoon Chinese Five Spice, divided
2 cups + 1/2 cup milk, divided
2 eggs
1/4 cup sugar
6 cups of cubed challah bread (about half a loaf)
1 gala or pink lady apple
1/2 cup dried cherries
2 teaspoons fresh rosemary, roughly chopped
Kosher salt
Freshly ground black pepper
To Make the Squash
Preheat your oven to 375F.
Place a large piece of parchment paper on a baking sheet and reserve.
Slice the butternut squash lengthwise, and scoop out the seeds & stringy flesh with a large spoon.
Place the squash halves on the prepared baking sheet.
Melt 1 tablespoon of butter in the microwave, in a microwave safe bowl.
Combine the 1/4 teaspoon of ground cinnamon, 1/4 teaspoon of Chinese Five Spice, and 1 tablespoon of light brown sugar, with a generous pinch of kosher salt & pepper in a small bowl. Stir gently to combine.
Using a small pastry brush, apply the melted butter to the squash halves and sprinkle the brown sugar/spice mix evenly on top. Try to cover as much of the squash as you can.
Place the baking sheet on the middle rack in the preheated oven and bake for 40-50 minutes, or until a knife can slide easily into the cooked squash.
After cooking, remove from the oven and let the butternut squash cool for 10 minutes.
Keep your oven on.
To Make the Custard
Using a large saucepan, combine the 2 cups of milk with the 1/4 cup of sugar, 1/8 teaspoon of Chinese Five Spice, and a pinch of kosher salt & pepper. Stir.
Next, add 3 tablespoons of cold butter to the milk and place the pot on medium heat.
Slowly warm until the butter has just melted, while stirring occasionally.
Remove from the heat.
Fork whisk the eggs in a small bowl and then whisk into the slightly cooled milk mixture. Reserve.
After the squash has cooled, scoop out the cooked flesh into a blender and add the reserved 1/2 cup of milk.
Blend until smooth. If you need more liquid to create a smoother puree consistency, add a bit of the custard mixture to the blender.
Add the blended squash to the pot containing the custard mix. Whisk thoroughly to combine. Reserve.
To Assemble
Butter a large casserole dish or several ramekins, if you are making individual portions.
Peel and core your apple. Then, thinly slice. Reserve.
Roughly cube or hand tear your challah bread, measuring about 6 cups. Reserve.
Now, we will begin to layer our ingredients; spread several slices of apple on the bottom of your dish as the base, then layer some of the cubed bread, and a sprinkle of the dried cherries. Repeat the layers until your vessel is full. End with a bread layer on top.
Sprinkle on the roughly chopped rosemary.
Next, gently ladle the butternut squash custard over the bread mixture, or portion it evenly between your ramekins if you are choosing to serve individual portions. You want to keep adding the custard liquid until it comes up 3/4 of the way up the side.
Gently press the bread cubes down into the custard to make sure they are well coated.
Let sit for 5 minutes, and then transfer to the hot oven.
Once in the oven, lower the temperature to 350F.
Bake for 30-35 minutes, or until the custard is just set and is pulling away from the edges of the dish.
Remove and let cool for 10 minutes before serving.

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