Roast the squash: Preheat oven to 400° F. Line a rimmed baking sheet with parchment paper. Place cubed squash in a large mixing bowl. Drizzle on 1 ½ tablespoons of olive oil. Sprinkle with ¼ teaspoon sea salt and ⅛ teaspoon pepper. Toss to coat the squash with the oil and seasonings. Spread the squash out on the baking sheet in a single layer with a bit of room in between each piece. Bake for 15 minutes, then use a spatula to flip the squash pieces and continue baking for 10-15 more minutes, until squash is tender when pierced with a fork and lightly browned on the edges.
3 pound butternut squash, 1 ½ tablespoons olive oil, ¼ teaspoon fine sea salt, ⅛ teaspoon black pepper
Meanwhile, cook the pasta: Bring a large pot of salted water to a boil. Once boiling, add the pasta and cook according to package directions for al dente. Reserve ½ cup of the pasta cooking water, then drain the pasta (do not rinse).
1 pound orecchiette pasta
While the pasta cooks: Heat 1 tablespoon of olive oil in a large skillet over medium-high heat. Add the sausage (first remove it from the casings if sold in casings), crumble and cook until cooked through.
1 tablespoon olive oil, 1 pound Italian sausage
Once the sausage is fully cooked, reduce the heat to medium and add the butter and shallot to the pan. Cook, stirring, for 2 minutes. Then add the chopped fresh sage and cook for 1 minute.
1 tablespoon unsalted butter, ½ cup chopped shallot, 6 leaves fresh sage
Add the minced garlic and chopped spinach and cook, stirring, for 1 minute, until spinach wilts. Add the cooked pasta, 2 tablespoons of the reserved pasta cooking water, and some salt and pepper, to taste. If the pasta seems dry, stir in 1 more tablespoon of pasta cooking water. Last, gently mix in the roasted butternut squash.
2 cloves garlic, 3 cups chopped fresh spinach, salt and pepper
Serve, with grated Parmesan and a few pinches of red pepper flakes, if desired.