Roasted Acorn Squash Stuffed with Chestnuts, Apples, and Leeks

These roasted acorn squash halves are filled with a savory-sweet stuffing of chestnuts, apples, leeks, and rye bread, making a festive vegetarian main or a hearty side for holiday roasts.

This dish turns acorn squash into edible bowls, roasted until tender and filled with a rich, aromatic stuffing. The combination of sweet apples, earthy chestnuts, and savory leeks, bound with cream and stock, creates a satisfying balance of flavors and textures.

Perfect for Thanksgiving, Christmas, or any winter gathering, these stuffed squash halves can stand alone as a vegetarian main course or accompany roasted meats. The rye bread adds a pleasant chewiness and helps absorb the delicious juices during baking.

Ingredients

Servings 8

Converted amounts are rounded.

Method

  1. Preheat the oven to 350°F. Brush the cut sides of the squash with olive oil and season the cavities with salt and pepper. Place the squash cut side down on two baking sheets and roast for about 25 minutes, until just tender.
  2. Meanwhile, in a large skillet, melt the butter in the 3 tablespoons of olive oil. Add the celery, leeks, and a generous pinch each of salt and pepper. Cook over moderate heat, stirring occasionally, until softened, about 8 minutes. Add the apples and thyme and cook over moderately high heat until the apples just start to soften, about 5 minutes. Scrape the mixture into a large bowl.
  3. Add the bread cubes, chestnuts, parsley, heavy cream, and vegetable stock to the bowl. Toss well to combine. Season with salt and pepper to taste.
  4. Turn the squash cut side up. Spoon the stuffing into the cavities, mounding it slightly. Bake until the squash are tender and the stuffing is golden brown, about 20 minutes. Transfer to plates and serve.

💡 Tips

  • For a vegan version, substitute the butter with olive oil and use a plant-based cream.
  • If you can't find vacuum-packed chestnuts, you can roast fresh chestnuts and peel them.
  • The stuffed squash can be assembled a few hours ahead and baked just before serving.

Inspired by a recipe from Food & Wine

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