Preheat the oven to 400°F (200°C), and prepare a baking sheet with parchment paper or aluminum foil.

Cut the butternut squash in half lengthwise and scoop out the seeds using a spoon. Place the butternut squash cut side up and drizzle with 2 tablespoons of olive oil and sprinkle with the salt and pepper. Turn the squash over and place them cut side down on the baking sheet.

Roast the squash in the preheated oven for 30-35 minutes, or until the flesh is tender when pierced with a fork.

While the squash is roasting, heat 2 tablespoons of olive oil in a large skillet over medium heat.

Add the diced onion and cook until it becomes soft and translucent, about 5 minutes. Add the spicy italian sausage to the skillet, breaking it up with a wooden spoon as it cooks. Cook until fully browned and cooked through, about 7-10 minutes.

Stir in the minced garlic, oregano, and allspice, continue cooking for another minute until fragrant.

Add the chopped spinach, diced apples, and chicken stock to the skillet and cook until the spinach is wilted and the apples have softened, about 2-3 minutes. Mix in the dried cranberries, and chopped pecans. Add the parmesan cheese and stir until well combined.

Remove the butternut squash from the oven and flip them over so the cut side is facing up. Scoop out the flesh leaving a ½” border around the squash. Save the flesh for another use or you can mash and mix it into the sausage mixture.

Spoon the sausage mixture evenly into each squash half, pressing down slightly to pack the filling in.

Return the squash halves to the oven and bake for an additional 10-15 minutes, until everything is heated through and the tops are slightly golden brown.

Remove the squash from the oven and allow them to cook slightly before serving. Enjoy!