Bread pudding usually belongs on the dessert table, but this version makes a strong case for moving it to dinner. Anna Franklin, TABLE‘s food stylist and recipe developer, fills roasted winter squash halves with a rich, savory bread pudding of browned sweet Italian sausage, tender brioche, fresh sage and thyme, and a spoonful of black truffle paste. The custard puffs and sets in the oven while the top turns golden and crisp, and every bite balances earthy, heady truffle with the gentle sweetness of roasted squash.
It’s a dish that works on almost any fall or winter table. Serve it as an impressive holiday side, or pair it with a crisp mixed greens salad for a cozy weeknight dinner. It’s also a sneaky way to get kids to eat their vegetables: roasting turns squash soft, sweet, and much easier to love, and few children will turn down anything that tastes like sausage and buttery bread.
What Is the Best Squash for Stuffing?
Small to medium winter squash with a natural hollow work best, since each half becomes its own edible bowl. Anna suggests delicata, acorn, or red kabocha. Delicata is slender with a thin, edible skin, so there’s no need to peel it, and it cooks fastest. Acorn squash has deep ridges and a generous cavity that holds plenty of filling. Red kabocha, also called red kuri, has dense, chestnut-sweet flesh that pairs beautifully with truffle. Mixing two or three varieties on one platter makes for a striking, colorful presentation at a holiday table.
Halve the squash, scoop out the seeds and stringy centers, and set the halves cut side up on a baking sheet. Drizzle with olive oil, season with salt and pepper, and roast at 350°F until the flesh is fork-tender, about 35 to 45 minutes depending on size and variety.
How Do You Make Savory Bread Pudding Stuffing?
While the squash roasts, brown a pound of sweet Italian sausage in a large skillet, breaking it into small pieces so it spreads evenly through the bread. Transfer it to a large bowl. Cut eight slices of brioche into 1-inch cubes and toss them with the sausage. Brioche, enriched with eggs and butter, soaks up custard like a sponge and bakes up tender with crisp, caramelized edges.
In a separate bowl, whisk three eggs with two cups of heavy cream, chopped fresh sage and thyme, black truffle paste, salt, and pepper. Start with one tablespoon of truffle paste and add more if you love its intense, earthy aroma. Jarred truffle paste is sold at specialty grocers and Italian markets, and a little goes a long way.
Pour the custard over the bread and sausage and fold gently until every cube is moistened. Then spoon it into the roasted squash halves, mounding it generously, and bake for 20 to 25 minutes, until the tops are browned and crisp and the custard is set. Bake any extra filling in a small buttered dish alongside the squash.
Tips for Recipe Success
Use day-old brioche. Slightly stale bread absorbs more custard without falling apart. If your loaf is fresh, dry the cubes in a 300°F oven for about 10 minutes first.
Let the bread soak. Give the custard-soaked cubes about 10 minutes to drink in the liquid before filling the squash, so the pudding bakes up creamy rather than dry in spots.
Steady the squash. If a half wobbles, trim a thin slice from its rounded side so it sits flat and the filling stays put.
Mound, don’t pack. Spoon the filling in loosely so the custard can puff and set evenly.
Can I Make This Stuffed Squash Recipe Ahead of Time?
Roast the squash and brown the sausage up to a day ahead, then refrigerate them separately. Assemble the bread pudding and fill the squash just before baking, adding a few extra minutes since everything starts out cold. Garnish with rosemary sprigs and crushed red peppercorns for a festive finish.
Can I Use Truffle Oil Instead of Truffle Paste?
Yes, with a light hand. Truffle oil is far more concentrated, and most brands are flavored rather than made with real truffles, so start with about a teaspoon whisked into the custard, then taste and adjust. Paste adds texture and a rounder earthiness that oil can’t quite match. For a truffle-free version, stir a handful of finely chopped sautéed mushrooms into the bread mixture, or simply leave the truffle out; the sausage, herbs, and cream still deliver plenty of flavor. If you can’t find brioche, challah is the closest substitute.
What Dietary Swaps Can You Make for This Recipe?
Gluten-free: Replace the brioche with a gluten-free brioche or soft gluten-free sandwich bread, and check that your sausage and truffle paste are labeled gluten-free.
Dairy-free: Use full-fat canned coconut milk or an unsweetened plant-based creamer in place of the heavy cream, and choose a dairy-free bread, since brioche is made with butter and milk.
What Can I Serve With Bread Pudding Stuffed Squash?
A mixed greens salad with a sharp vinaigrette cuts through the richness and turns the squash into a complete meal. At a holiday dinner, serve it alongside roast turkey, pork tenderloin, or roast chicken.
Explore TABLE‘s Cozy Fall and Winter Squash Recipes, or set this dish beside two more stuffing favorites: Cheryl Alters Jamison’s Ultimate Stuffing Recipe and Quelcy Kogel’s Inspired Holiday Stuffing.
Cheryl’s Baked Apples with Sausage Stuffing and Baked Baby Pumpkins offer more ways to turn seasonal produce into a stuffed showpiece.
Planning a holiday spread? Browse our Thanksgiving Finger Foods, Mac and Cheese Recipes for a Cozy Kitchen, and Side Dishes.
Print
Bread Pudding Stuffed Squash with Savory Black Truffle
- 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
- 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
- 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.
- 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.
- Cut the brioche into 1-inch cubes and toss with the sausage.
- In a separate bowl, whisk together the eggs, cream, sage, thyme, truffle paste, salt, and pepper.
- Pour the egg mixture over the bread and sausage and fold gently until the bread is fully moistened. Let stand 10 minutes.
- 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.
- 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
About the Recipe Author and Stylist
Anna Franklin is TABLE Magazine‘s food stylist and recipe developer. A Pittsburgh native and graduate of the Indiana University of Pennsylvania Academy of Culinary Arts, she spent years in restaurant kitchens and photo studios before turning to food styling. She is also the founder of Bazaaa Sauce, a Pittsburgh hot sauce microbrand. Read more of her recipes at TABLE.
About the Photographer
Dave Bryce is TABLE Magazine‘s principal photographer. Known for images that explore depth and dimension through space and light, he is also a commercial and editorial food photographer who works closely with chefs and food stylists. See more of his work in TABLE Magazine.
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