Preheat the oven to 400°. Line a large, rimmed baking sheet with parchment paper.
Trim the ends from the delicata squash, and slice it in half lengthwise. Remove the seeds. Slice each half lengthwise into 1½ inch planks. (Depending on the width of your squash, you’ll have 2-3 planks.) Slice the planks crosswise into ½-inch thick pieces. Place the squash in a large mixing bowl. Drizzle with 1 tablespoon of the olive oil, maple syrup, cinnamon, and ¼ teaspoon of the kosher salt, and toss to coat.
Spread the squash on the prepared baking sheet, leaving a little bit of space between each piece. Roast for 15 minutes, then give the squash a stir. Roast for 5 minutes more or until tender (but not mushy!).
Meanwhile, place the pepitas in a medium saucepan (no oil should be in the pan) over medium heat. Toast for 2 to 3 minutes, shaking the pan occasionally, until lightly browned in spots and fragrant. Transfer to a plate or bowl to cool.
In the same saucepan you used for the pepitas, heat the remaining 1 tablespoon of olive oil over medium heat. When the oil is hot and shimmering add the couscous and the remaining ½ teaspoon of kosher salt. Cook for 2 minutes until the couscous is lightly browned in spots and toasted. Pour in the water and bring to a boil. Immediately lower to a simmer, cover the pan with a lid, and cook for 8-10 minutes or until all the liquid has been absorbed. Give the couscous a good stir and add it to the mixing bowl you used for the squash. (No need to clean the bowl first.) Let the couscous cool to room temperature, stirring occasionally to prevent clumping.
In a medium bowl, whisk all the ingredients for the dressing. Add the sliced apple to the bowl with the dressing and toss to coat. (This will ensure that the apple doesn't brown over time.)
Add the dressing and apple to the bowl with the couscous and toss to combine. Add the scallions, roasted squash, toasted pepitas, and cranberries or pomegranate arils, and toss again. Taste and season with additional salt and pepper if needed.
Transfer to a serving bowl or platter if you like and top with the cheese (if using). Serve slightly warm or at room temperature.