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1
Put oven rack in middle position and preheat oven to 450F.
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2
Line a large shallow baking pan with foil and oil generously with olive oil.
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3
Cut off stem end of squash, then put cut side down and halve lengthwise.
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4
Discard seeds, then cut squash into 1/2-inch-thick slices.
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5
Peel if desired with a paring knife and transfer slices to a bowl.
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6
Add 1 tablespoon olive oil, 1/2 teaspoon salt, and 1/4 teaspoon pepper and gently toss to coat.
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7
Arrange in 1 layer in lined baking pan and roast until golden, about 15 minutes.
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8
Remove from oven and turn squash over with a spatula.
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9
Add chestnuts to pan in an even layer, then continue to roast until squash is golden and tender, 10 to 15 minutes.
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10
Keep warm, covered with foil.
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11
While squash is roasting, cook pancetta in a dry 10-inch heavy skillet over high heat until browned, about 4 minutes total.
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12
Transfer pancetta with a slotted spoon to paper towels to drain, reserving fat in skillet.
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13
Reheat pancetta fat over moderately high heat until hot but not smoking, then add cranberries and brown sugar and stir once to combine.
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14
Remove from heat and add water, stirring and scraping up brown bits from bottom of skillet.
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15
Transfer cranberry mixture to a medium bowl and whisk in mustard, remaining tablespoon olive oil, 1/2 teaspoon salt, and 1/4 teaspoon pepper.
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16
Toss together chicory, roasted acorn squash, and chestnuts.
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17
Just before serving, toss with dressing and sprinkle with pancetta.
