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Bread pudding stuffed squash halves on three blue plates, garnished with rosemary and red peppercorns.

Bread Pudding Stuffed Squash with Savory Black Truffle

  • Author: Anna Franklin
  • Total Time: 1 hour 25 minutes
  • Yield: 6 stuffed squash halves 1x

Description

Roasted winter squash halves filled with a savory bread pudding of sweet Italian sausage, brioche, fresh sage and thyme, cream, and black truffle paste, baked until golden and crisp.

Ingredients

Scale
  • 3 medium squash, such as delicata, acorn, or red kabocha, halved and seeded
  • Olive oil, for drizzling
  • 1 lb sweet Italian sausage, removed from casings
  • 8 slices brioche
  • 1 tbsp fresh thyme, chopped
  • 1 tbsp fresh sage, chopped
  • 3 eggs
  • 2 cups heavy cream
  • 1 to 2 tbsp jarred black truffle paste
  • 1 tsp salt, plus more for the squash
  • 1 tsp black pepper, plus more for the squash
  • Fresh rosemary sprigs and crushed red peppercorns, optional, for garnish

Instructions

  1. Preheat the oven to 350°F. Halve the squash and scoop out the seeds and centers. Place cut side up on a baking sheet, drizzle with olive oil, and season with salt and pepper. Roast until fork-tender, about 35 to 45 minutes.
  2. While the squash roasts, brown the sausage in a large pan over medium-high heat, breaking it into small pieces. Transfer to a large bowl.
  3. Cut the brioche into 1-inch cubes and toss with the sausage.
  4. In a separate bowl, whisk together the eggs, cream, sage, thyme, truffle paste, salt, and pepper.
  5. Pour the egg mixture over the bread and sausage and fold gently until the bread is fully moistened. Let stand 10 minutes.
  6. Spoon the mixture into the roasted squash halves and bake about 20 to 25 minutes, until the tops are browned and crisp and the custard is set.
  7. Serve hot, garnished with rosemary and red peppercorns, if desired.

Notes

Make ahead: Roast the squash and brown the sausage up to 1 day ahead; refrigerate separately. Assemble and fill just before baking, adding a few minutes to the bake time.

Truffle oil: Substitute about 1 tsp truffle oil for the paste, then taste and adjust. Challah can replace brioche.

Fresh bread: Dry fresh brioche cubes in a 300°F oven for about 10 minutes.

Extra filling: Bake any leftover bread pudding in a small buttered dish alongside the squash.

Gluten-free: Use gluten-free brioche or sandwich bread; check sausage and truffle paste labels.

Dairy-free: Use full-fat coconut milk or unsweetened plant-based creamer and a dairy-free bread.

Editor’s note: The original method calls for olive oil, salt, and pepper on the squash; olive oil has been added to the ingredient list. The 35-to-45-minute roasting time, 10-minute soak, and garnish are TABLE suggestions.

  • Prep Time: 20 minutes
  • Cook Time: 1 hour 5 minutes
  • Category: Side Dish
  • Method: Roasting and Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 stuffed squash half
  • Calories: 780

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