Toss squash, then return to one side of the baking sheet. Spread out ½ cup chopped raw walnuts in a single layer on the open side. Roast until squash is tender and nuts are golden brown, 5–10 minutes.

Meanwhile, bring a small saucepan of water to a boil. Using a slotted spoon, carefully lower 4 large eggs into water. Cook for 10 minutes. Transfer eggs to a bowl of ice water and let cool slightly. Remove from water; peel and chop. Set aside.

Whisk 3 Tbsp. balsamic vinegar, 2 Tbsp. pure maple syrup, 2 tsp. Dijon mustard, 1 tsp. kosher salt, and remaining ¼ cup extra-virgin olive oil in a measuring glass to emulsify (alternatively, shake vinaigrette in a small jar to combine).

Using tongs or your hands, toss 1 bunch Tuscan kale (ribs and stems removed, leaves thinly sliced) with 2 Tbsp. maple vinaigrette in a large bowl to coat. Taste and season with more salt if desired. Let sit for 10 minutes to allow kale to soften slightly.

Coarsely chop the bacon. Transfer kale to a platter and top with bacon, squash, walnuts, 1 medium apple (such as Honeycrisp or Gala), cored and chopped, 4 oz. extra-sharp cheddar (preferably aged), chopped, and reserved eggs. Pour remaining maple vinaigrette over; season with pepper.