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Toss the cubed winter squash and cherry tomatoes with olive oil and salt on a baking sheet; roast at 425 degrees F until tender, about 25 minutes.
Meanwhile, combine the farro or barley in a saucepan with ½ 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, about 15 to 20 minutes.
Drain the farro (remove the bay leaf) and toss with the roasted squash, tomatoes, 1 tablespoon olive oil, and 3 tablespoons each of chopped parsley and grated pecorino.
Season with salt and pepper.