Preheat oven to 400°F. Halve the squash lengthwise and scoop out the seeds. Brush cut sides with 1 tbsp olive oil, season with salt and pepper, and place cut-side down on a parchment-lined baking sheet. Roast 35-40 minutes, until a fork pierces the flesh easily.
Meanwhile, bring quinoa and 1 cup water to a boil in a small saucepan. Cover, reduce heat to low, and simmer 15 minutes. Remove from heat and let stand 5 minutes, then fluff with a fork.
Heat remaining 1 tbsp oil in a large skillet over medium-high. Add sausage and cook, breaking it up, 6-8 minutes until browned. Add onion and cook 3 minutes; stir in garlic for 30 seconds.
Add kale and cook 2-3 minutes until wilted. Remove from heat and fold in quinoa, cranberries and pecans; season with salt and pepper to taste.
Flip squash halves cut-side up and divide the filling among them, mounding slightly. Top with Parmesan if using.
Bake 10-12 minutes more, until the filling is hot and squash edges are golden. Serve warm.