Roast the squash: Preheat the oven to 400°F. Using a sharp knife, cut the squash in half crosswise. Cut a flat spot on the bottom so the squash halves sit flat. Using a spoon, scoop out the seeds and stringy pulp from the cavities. Place the squash halves, cut side up, on a baking sheet. Brush the squash with olive oil and season with salt and pepper. Roast for 30 minutes, or until just tender when pierced with a fork.
Meanwhile, make the stuffing. In a large skillet, heat 1 Tbs. of the oil over medium heat heat. Add the sausage, and cook stirring often, until lightly browned, about 3 minutes. Remove the sausage to a plate.
Heat the remaining oil in the skillet over medium high heat. Add the onion, pepper, celery and garlic and cook, stirring often, until softened, about 4 minutes. Add the apples, dried cranberries, thyme, sage, red pepper flakes, and salt and pepper to taste. Return the sausage to the skillet and stir in the quinoa and remove the pan from the heat.
Spoon the filling into the squash halves. In a small bowl, mix the breadcrumbs and Parmesan cheese. Sprinkle over the top.
Return the squash to the oven and bake until heated through and the panko mixture is lightly brown, about 15 minutes. Remove from the oven and serve with a drizzle of maple syrup.