Preheat the oven to 400°F (200°C).
Cut the acorn squashes in half and scoop out the seeds.
Brush the insides with olive oil, and sprinkle with salt and pepper.
Place the squashes cut-side down on a baking sheet.
Roast for 25-30 minutes until tender.
In a bowl, mix cooked quinoa, walnuts, cranberries, cinnamon, salt, and pepper.
Remove squashes from the oven and flip them cut-side up.
Fill each half with the quinoa mixture.
Drizzle with olive oil and return to the oven.
Bake for an additional 15 minutes until heated through.