1. Preheat oven to 375°F.
2. Peel squash (or use Delicata squash, unpeeled), remove seeds, cut into cubes. Toss with about half of the olive oil, sprinkle with salt and pepper and roast until tender, about 40 minutes. Cool slightly.
3. While the squash is roasting, cook the grain with broth in a medium covered saucepan, until the grains are tender but still chewy, about 25-30 minutes. Drain and cool slightly.
4. In a small bowl, whisk together vinegar, 1 Tablespoon water, Aleppo pepper, and sugar until sugar dissolves. Stir in the minced shallots. Cover and refrigerate the dressing until needed. (At least a half hour in the fridge deepens the flavor, but it’s still good if you’re in a rush.)
5. In a large bowl, combine the cooked squash, cooked grain, dressing, parsley, and cheese. Toss with the remaining olive oil. Serve warm, at room temperature, or chilled. Top with toasted pepitas at time of serving.

Note: you can buy pepitas already roasted, or buy raw ones and toast briefly in a hot, unoiled pan until they start to brown and “pop.”