Roasted Squash, Chestnut, and Chicory Salad with Cranberry Vinaigrette

Step 1

Put the oven rack in the middle position and preheat the oven to 450°F. Line a large shallow baking pan with foil and coat generously with olive oil.

Step 2

Cut off the stem end of the squash, then put cut side down and halve lengthwise. Discard the seeds, then cut the squash into 1/2-inch-thick slices. Peel if desired with a paring knife and transfer the slices to a bowl. Add 1 tablespoon olive oil, 1/2 teaspoon salt, and 1/4 teaspoon pepper and gently toss to coat. Arrange in a single layer in the lined baking pan and roast until golden, about 15 minutes. Remove from the oven and turn the squash over with a spatula. Add the chestnuts to the pan in an even layer, and continue to roast until squash is golden and tender, 10 to 15 minutes. Keep warm, covered with foil.

Step 3

Cook the pancetta in a dry 10-inch heavy skillet over high heat until browned, about 4 minutes total. Transfer the pancetta with a slotted spoon to paper towels to drain, reserving the fat in the skillet.

Step 4

Reheat the pancetta fat over moderately high heat until hot but not smoking, then add cranberries and brown sugar and stir once to combine. Remove from the heat and add the water, stirring and scraping up browned bits from bottom of skillet.

Step 5

Transfer the cranberry mixture to a medium bowl and whisk in the mustard, remaining tablespoon olive oil, remaining 1/2 teaspoon salt, and remaining 1/4 teaspoon pepper.

Step 6

Toss together the chicory, roasted acorn squash, and chestnuts. Just before serving, toss with dressing and sprinkle with pancetta.