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Stuffed Delicata Squash

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main coursesamericancontains meat, contains dairy, gluten-free
55 minutes4 servings

Ingredients

  • 2 medium delicata squashhalved lengthwise and seeded
  • 2 tbsp olive oil
  • 1 1/4 tsp kosher salt
  • 1/2 tsp black pepper
  • 12 ounces Italian sausagecasings removed (~4 medium italian sausages)
  • 1 small onionfinely chopped
  • 1 stalk celeryfinely chopped
  • 3 cloves garlicminced
  • 1 medium applepeeled and diced
  • 1 tbsp fresh sagefinely chopped
  • 1 tsp fresh thymechopped leaves
  • 1/4 tsp red pepper flakes
  • 1/4 cup chicken broth
  • 1/2 cup Parmesan cheesefinely grated
  • 2 tbsp fresh parsleychopped (for serving)
Stuffed Delicata Squash

Instructions

1. Heat the oven to 425°F. Place the delicata squash halves on a sheet pan, cut side up, and brush all over with 1 tbsp olive oil. Season with 0.5 tsp kosher salt and 0.25 tsp black pepper, then flip cut side down and roast until tender when pierced and edges are caramelized, 20–25 minutes.

2. Meanwhile, heat the remaining 1 tbsp olive oil in a large skillet over medium heat. Add the Italian sausage and cook, breaking it into small crumbles, until browned with little pink remaining, 5–7 minutes.

3. Add the onion and celery to the skillet and cook, stirring, until softened and translucent, 5–6 minutes. Stir in the garlic, fresh sage, fresh thyme, and red pepper flakes; cook until fragrant, 30–60 seconds.

4. Add the apple and cook until slightly softened, 2–3 minutes. Pour in the chicken broth, scraping up any browned bits. Add the kale and cook, stirring, until wilted and most of the liquid has evaporated, 3–5 minutes.

5. Season the filling with the remaining 0.75 tsp kosher salt and 0.25 tsp black pepper. Remove from the heat and stir in the Parmesan cheese until evenly combined.

6. Turn the roasted squash cut side up. Pack the sausage mixture firmly into each cavity, mounding slightly.

7. Return the stuffed squash to the oven and bake until heated through and the tops look lightly browned, 10–12 minutes. For deeper color, broil 1–2 minutes, watching closely.

8. Let rest 5 minutes. Sprinkle with the fresh parsley and serve warm.

Stuffed Delicata Squash pairs the naturally sweet, creamy flesh of delicata with a savory, herb-scented filling for a balanced, cool-weather main. The squash’s thin, edible skin roasts to tenderness, while the cavity holds a hearty mixture that often includes sausage, aromatics, and leafy greens. The result is a satisfying contrast of caramelized squash, juicy, well-seasoned filling, and a bit of richness from cheese.

Delicata squash is a North American heirloom winter squash prized for its ease—no peeling required—and honeyed flavor. While stuffing vegetables is a global technique, delicata’s boat-like halves made it a natural canvas in modern American seasonal cooking. Contemporary versions have evolved to showcase fall pantry staples and herbs, reflecting farmers’ market cooking and the broader rise of vegetable-forward main courses.