Steps:
- Meanwhile, bring a large pot of salted water to a boil over high heat. Add the brussels sprouts and cook until just tender, 4 to 6 minutes. Using a slotted spoon, transfer the brussels sprouts to a bowl of ice water. Drain well, then cut them in half lengthwise and place on a paper towel-lined baking sheet. Return the water in the pot to a boil, add the butternut squash and cook until just tender, 4 to 6 minutes. Drain, then transfer to a bowl of ice water. Drain again and place on a paper towel-lined baking sheet. In a large sauté pan over medium heat, warm the remaining 1 Tbs. olive oil. Add the squash and sauté, stirring occasionally, until light golden and warmed through, 3 to 4 minutes. Transfer to a large bowl. In the same pan over medium-high heat, warm 2 Tbs. of the reserved bacon fat. Place the brussels sprouts, cut side down, in the pan. Cook, without moving them, for 3 to 4 minutes, then stir and add the sage and chestnuts. Cook for 2 minutes more. Transfer to the bowl with the squash. Add enough vinaigrette to lightly coat the vegetables (you may not need all of it), then stir in half of the bacon. Transfer the vegetables to a platter, sprinkle with the remaining bacon and serve immediately.
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