INGREDIENTS
- 2 medium shallots, trimmed, peeled, and halved
- 3 medium garlic cloves, peeled
- 1/4 cup plus 2 tablespoons olive oil
- 8 ounces day-old crusty bread, such as pain au levain, cut into 1/2-inch cubes (about 6 cups)
- 3 pounds butternut squash, peeled, seeded, and cut into 1/2-inch cubes (about 6 cups)
- 1/2 teaspoon ground sage
- 3 tablespoons balsamic vinegar
- 1 teaspoon honey
- 1/4 teaspoon kosher salt, plus more for seasoning
- 1/8 teaspoon freshly ground black pepper, plus more for seasoning
- 1/2 cup dried cranberries
- 1/2 cup walnuts, toasted and coarsely chopped
INSTRUCTIONS
- Heat the oven to 400°F and arrange a rack in the middle.
- Place the shallots and garlic on an 8-inch-long piece of foil and drizzle with 1 tablespoon of the oil. Bring the sides of the foil together and tightly fold down to seal into a packet. Place directly on the oven rack and roast until the shallots and garlic are softened and browned, about 45 minutes.
- Meanwhile, toast the bread and roast the squash: Place the bread in a single layer on a baking sheet. 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. Remove the bread to a large bowl and set aside. Wipe any crumbs off the baking sheet; set the sheet aside. Leave the foil packet off to one side of the oven rack.
- Place the squash in a second large bowl. Add the sage and 1 tablespoon of the oil, and season generously with salt and pepper. Toss until the squash pieces are evenly coated. Transfer the squash to the reserved baking sheet and spread into an even layer. Roast next to the foil packet for 15 minutes. Using a flat metal spatula, stir the squash, scraping it up from the baking sheet and spreading it back into an even layer. Continue roasting until the squash is browned on one or two sides and fork tender, about 10 to 15 minutes more. Place the baking sheet on a wire rack; set aside.
- When the shallots and garlic are ready, remove the foil packet from the oven and carefully open it. Transfer the shallots and garlic to a blender and add the vinegar, honey, and measured salt and pepper. Cover and blend on high speed until smooth. 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. Leave the vinaigrette in the blender.
- Add the roasted squash, cranberries, and walnuts to the bowl with the bread. Drizzle with the vinaigrette and toss until all of the ingredients are well coated. Let sit at room temperature until the flavors meld and the bread softens slightly, at least 10 minutes. Serve warm or at room temperature.