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Preheat your oven to 400°F (200°C). Line a baking sheet with parchment paper.
Cut the butternut squashes in half lengthwise and scoop out the seeds. Brush the flesh with olive oil and season with salt and pepper. Place the squash halves cut side down on the baking sheet. Roast for 40-50 minutes, or until the flesh is tender.
While the squash is roasting, heat a large skillet over medium heat. Add the turkey sausage and cook until browned, breaking it up into small pieces. Remove from the skillet and set aside.
In the same skillet, add the diced onion and cook until softened. Add the minced garlic and cook for another minute. Stir in the fresh spinach and cook until wilted.
In a large bowl, combine the cooked sausage, sautéed onions and spinach, dried cranberries, chopped pecans, dried sage, dried thyme, dried rosemary, and red pepper flakes. Mix well to combine.
Once the squash is roasted and tender, remove from the oven and flip them over. Spoon the sausage mixture into the cavities of each squash half, pressing down gently to pack the filling.
Return the stuffed squashes to the oven and bake for an additional 10-15 minutes, until the filling is heated through and slightly crispy on top.
Remove from the oven and let cool slightly before serving.