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Preheat oven to 425°F. Line a shallow baking pan with foil. In a large bowl toss together squash and 1 tablespoon of the oil. Transfer squash to the foil-lined baking pan. Roast for 10 minutes. Stir squash and push to one side of the pan. Toss mushrooms in remaining 1 tablespoon olive oil. Place mushrooms on other side of pan. Roast about 15 minutes or until squash is just tender and mushrooms are roasted. Reduce oven temperature to 350°F.
Meanwhile, in a large saucepan, bring water to a boil; add farro. Return to boiling; reduce heat. Simmer, covered, for 25 to 30 minutes or until just tender; drain.
In a very large skillet, cook and stir pancetta over medium-high heat until crisp. Using a slotted spoon, transfer pancetta to paper towels to drain. Add onion, celery, and garlic to drippings in skillet. Cook over medium heat, about 3 minutes or until vegetables are tender, stirring occasionally. Add wine, half-and-half (or cream), thyme, rosemary, salt and pepper to skillet. Bring to a boil. Add squash to skillet and mash slightly to make sauce-like consistency. Stir in cheese until melted. Stir in drained farro, mushrooms and pancetta, tossing to combine. Transfer stuffing to a buttered 2-quart casserole or baking dish. Cover with foil. Bake about 20 minutes or until heated through.