Toss 2 cups cubed winter squash and 1 pint cherry tomatoes with olive oil and salt on a baking sheet; roast at 425 degrees F until tender, 25 minutes. Meanwhile, combine 1 cup farro or barley in a saucepan with 1/2 teaspoon salt, a pinch of red pepper flakes, a bay leaf and enough water to cover by 1 inch. Bring to a simmer over high heat, then reduce the heat to medium low and cook, uncovered, until al dente, 15 to 20 minutes. Drain the farro (remove the bay leaf) and toss with the squash, tomatoes, 1 tablespoon olive oil and 3 tablespoons each chopped parsley and grated pecorino. Season with salt and pepper.