Start by preheating your oven to 375°F (190°C). Slice the butternut squash in half lengthwise and scoop out the seeds. Rub the cut sides with a little olive oil and sprinkle with salt and pepper for seasoning. Place the squash face-down on a baking sheet and roast for 40 minutes, or until tender.
While the squash is roasting, heat up a skillet over medium heat. Add the ground sausage and cook until it’s fully browned, breaking it into smaller crumbles as it cooks.
Grab a mixing bowl and combine the cooked sausage, chopped spinach, pecans, cranberries, minced garlic, Parmesan cheese, and seasonings (thyme, sage, nutmeg). Stir everything until it’s evenly mixed, and your filling is ready to go!
Once the squash is tender, take it out of the oven and allow it to cool slightly. Use a spoon to carefully scoop out some of the flesh from each half to make a hollow “bowl.” Don’t waste the scooped-out flesh; you can mash it into the filling for extra flavor!
Fill the hollowed-out squash halves with the sausage mixture, pressing it down gently as you go. Return the stuffed squash to the oven and bake for another 15–20 minutes, or until the filling is golden brown and piping hot.