Heat the oven to 400 degrees F. Place the four acorn squash halves cut-side up on a large rimmed baking sheet. Brush the cut surfaces with 1 tablespoon of olive oil and sprinkle with 1/4 teaspoon salt and the black pepper. Flip them cut-side down onto the pan. Roast for 30 to 35 minutes until the squash is tender when pierced through the skin with a fork and the cut sides have turned golden where they touched the pan. Set aside to cool for 10 minutes.

While the squash roasts, cook the quinoa. Rinse it in a fine mesh strainer under cold water for 30 seconds, then add it to a medium saucepan with the vegetable broth. Bring to a boil over medium-high heat, reduce to a low simmer, cover, and cook for 15 minutes. Remove from heat and let it sit covered for 5 minutes, then fluff with a fork. The quinoa should look like it has little white rings around each grain. That means it is fully cooked.

Make the maple-mustard dressing. In a small bowl, whisk together the maple syrup, Dijon mustard, apple cider vinegar, the remaining 2 tablespoons olive oil, cinnamon, cumin, and the remaining 1/2 teaspoon salt until fully combined and smooth.

Once the squash is cool enough to handle, use a large spoon to scoop the flesh from the skins into a large mixing bowl. Break it into rough chunks, not a smooth puree. Some texture is good here. Add the cooked quinoa, dried cranberries, and pepitas. Pour the maple-mustard dressing over everything and fold gently to combine. Taste and add more salt if needed. Quinoa can absorb a lot of seasoning, so do not be shy here.

Lower the oven temperature to 375 degrees F. Lightly grease a shallow 2 quart baking dish with olive oil. Spread the quinoa and squash mixture evenly into the dish and press the top gently with the back of a spoon to level it.

Bake uncovered for 15 to 20 minutes until the edges are lightly set and the top feels dry to the touch rather than wet. The purpose of this final bake is to bring everything together and warm it through, not to cook it further. Remove from the oven and let it rest for 5 minutes. Scatter the chopped parsley or sage over the top and serve directly from the dish.