Tender roasted butternut squash halves are filled with savory spicy Italian sausage, wilted spinach, sweet apple, tart cranberries, and crunchy walnuts. This cozy, colorful main dish is easy enough for a weeknight and festive enough for a holiday table.
Heat the oven to 400°F (200°C) and prepare a baking sheet.
Slice the butternut squash in half lengthwise and scoop out the seeds. Brush the cut sides with ½ tablespoon olive oil, then season with salt and black pepper.
Place the squash halves cut side up on the baking sheet. Roast for 40–45 minutes, until the flesh is fork-tender.
While the squash roasts, heat the remaining ½ tablespoon olive oil in a large skillet over medium-high heat. Add the crumbled sausage and cook until browned, seasoning lightly with salt and pepper.
Add the diced onion and minced garlic to the skillet. Sauté for about 3 minutes, until the onion is softened and translucent.
Stir in the spinach and cook for 2–3 minutes, until wilted. Add the chopped apple and Italian seasoning, then cook for another 2–3 minutes, until the apple begins to soften.
Remove the skillet from the heat and stir in the dried cranberries and chopped walnuts.
Remove the squash from the oven. If needed, use a fork to scoop out a little flesh to make room for the filling. Spoon the sausage mixture into the squash halves.
Garnish with fresh thyme, if desired, and serve warm.