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1
Heat the oven to 400 degrees F and arrange a rack in the middle.
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2
Place the shallots and garlic on an 8-inch-long piece of foil and drizzle with 1 tablespoon of the oil.
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3
Bring the sides of the foil together and tightly fold down to seal into a packet.
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4
Place directly on the oven rack and roast until the shallots and garlic are softened and browned, about 45 minutes.
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5
Meanwhile, toast the bread and prepare and roast the squash: Place the bread in a single layer on a baking sheet.
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6
Move the foil packet aside on the oven rack as necessary, place the bread in the oven, and bake until toasted, about 6 to 8 minutes.
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7
Remove the bread to a large bowl and set aside.
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8
Wipe any crumbs off the baking sheet and set it aside.
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9
Leave the foil packet off to one side of the oven rack.
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10
Prepare the squash: Peel off the skin with a vegetable peeler.
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11
Trim the top and bottom.
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12
Cut the neck from the bulb of the squash.
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13
Halve each piece lengthwise and scrape out the seeds.
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14
Cut the squash into 1/2-inch cubes and place in a large bowl.
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15
Add the sage and 1 tablespoon of the oil, and season generously with salt and pepper.
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16
Toss until the squash pieces are evenly coated.
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17
Transfer the squash to the reserved baking sheet and spread into an even layer.
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18
Roast next to the foil packet for 15 minutes.
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19
Using a flat metal spatula, stir the squash, scraping it up from the baking sheet and spreading it back into an even layer.
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20
Continue roasting until the squash is browned on one or two sides and fork tender, about 10 to 15 minutes more.
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21
Place the baking sheet on a wire rack; set aside.
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22
When the shallots and garlic are ready, remove the foil packet from the oven and carefully open it.
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23
Transfer the shallots and garlic to a blender and add the vinegar, honey, and measured salt and pepper.
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24
Cover and blend on high speed until smooth.
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25
With the motor running, remove the small cap from the blender lid, slowly add the remaining 1/4 cup of oil in a thin stream, and blend until smooth.
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26
Leave the vinaigrette in the blender.
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27
Add the roasted squash, cranberries, and walnuts to the bowl with the bread.
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28
Drizzle with the vinaigrette and toss until all of the ingredients are well coated.
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29
Let sit at room temperature until the flavors meld and the bread softens slightly, at least 10 minutes.
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30
Serve warm or at room temperature.
