Stuffed acorn squash is one of those fall dishes that manages to feel both fancy and completely doable on a weeknight. You get sweet, caramelized squash halves loaded with a savory sausage, wild rice, and apple filling, all finished with toasted pecans and a hit of dried cranberries. It works as a hearty side next to roast chicken or turkey, and it's substantial enough to serve as the main event for a vegetarian-friendly dinner if you swap out the sausage.
Large rimmed baking sheet lined with aluminum foil for easier cleanup
Large cast iron skillet or heavy-bottomed pan
Sharp chef's knife essential for safely halving the squash
Cutting board stable and large enough for squash
Large mixing bowl
Aluminum foil for lining the pan and tenting if needed
Measuring cups and spoons
Enameled cast iron baking dish optional, helps squash roast evenly and looks great for serving
Ingredients
2medium acorn squashhalved and seeded
2tablespoonsolive oil30 ml, divided
Saltto taste
Freshly ground black pepperto taste
1poundItalian sausage455g, casings removed
1cupwild riceabout 240ml, cooked according to package directions
1medium yellow oniondiced
2celery stalksdiced
2garlic clovesminced
1medium applesuch as Honeycrisp or Granny Smith, cored and diced
1/3cupdried cranberriesabout 80ml
1/3cuppecansabout 80ml, toasted and chopped
1teaspoonfresh sagechopped, or 1/2 teaspoon dried sage
1/2teaspoonfresh thyme leaves
1/4cuplow sodium chicken brothabout 60ml, or vegetable broth
1/4cupParmesan cheeseabout 60ml, grated, optional
Instructions
Preheat oven to 400°F and line a large rimmed baking sheet with foil. Halve the squash lengthwise, scoop out the seeds, and trim a thin sliver off the bottom if needed so they sit flat.
Brush cut sides with 1 tablespoon olive oil and season generously with salt and pepper. Place cut side down on the baking sheet and roast for 35-40 minutes until tender but still holding their shape.
Heat the remaining 1 tablespoon olive oil in a cast iron skillet over medium heat. Cook the sausage, breaking into crumbles, for 6-8 minutes until browned. Transfer to a large bowl with a slotted spoon.
In the same skillet, cook onion and celery for 5-6 minutes until translucent. Add garlic and cook 30 seconds. Stir in apple, sage, and thyme, and cook for 3-4 minutes until apple softens slightly.
Combine cooked wild rice with the sausage in the bowl. Add the sautéed vegetables, cranberries, pecans, and broth. Stir well and season with salt and pepper to taste.
Arrange the roasted squash cut side up and divide the stuffing among the four cavities, mounding slightly. Sprinkle with Parmesan cheese if using.
Return stuffed squash to the oven and bake for 15-20 minutes until golden and heated through. Tent with foil if the tops brown too quickly.
Let the squash rest for 5 minutes before serving. Serve warm, one half per person.
Notes
Choose squash that feel heavy for their size with hard, unblemished skin for the best texture and flavor.
Don't skip the initial roast; pre-cooking the squash prevents a soggy, undercooked base.
Toast the pecans in a dry skillet for a few minutes before adding them to the stuffing for a deeper, nuttier flavor.
Let the sausage brown properly with good color before moving on to the vegetables for maximum flavor.
Taste the stuffing mixture before filling the squash — this is your last chance to adjust salt and pepper.
To make ahead, roast the squash and prepare the stuffing separately up to a day in advance. Assemble and bake just before serving.
Store leftovers in an airtight container in the refrigerator for up to 4 days. Reheat in a 350°F oven covered with foil for 15 minutes or microwave individual portions for 1-2 minutes.
To freeze, wrap cooled, stuffed squash halves tightly in foil and freeze for up to 2 months. Thaw overnight in the fridge before reheating.
For a vegetarian version, skip the sausage and add extra wild rice, mushrooms, or a can of drained white beans with a splash of soy sauce or extra broth.
Acorn squash skin is edible once roasted and becomes soft enough to eat, though most people scoop out the flesh and leave the skin on the plate.