Step 1
Preheat oven to 425°. Toss 1 lb. precut ½” pieces butternut squash and 2 Tbsp. extra-virgin olive oil on a rimmed baking sheet to coat; season with kosher salt and freshly ground pepper. Push squash to one side and arrange 4 thick-cut bacon slices on other side. Bake until bacon is lightly browned, 9–12 minutes. Turn bacon over and continue to bake until crisp, 5–10 minutes more. Transfer bacon to a plate.
Step 2
Toss squash, then return to one side of baking sheet. Spread out ½ cup chopped raw walnuts in a single layer on open side. Roast until squash is tender and nuts are golden brown, 5–10 minutes.
Step 3
Meanwhile, bring a small saucepan of water to a boil. Using a slotted spoon, carefully lower 4 large eggs into water. Cook 10 minutes. Transfer eggs to a bowl of ice water and let cool slightly. Remove from water; peel and chop. Set aside.
Step 4
Whisk 3 Tbsp. balsamic vinegar, 2 Tbsp. pure maple syrup, 2 tsp. Dijon mustard, 1 tsp. Diamond Crystal or ½ tsp. Morton 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).
Step 5
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 10 minutes to allow kale to soften slightly.
Step 6
Coarsely chop bacon. Transfer kale to a platter and top with bacon, squash, walnuts, 1 medium apple (such as Honeycrisp or Gala), cored, chopped, 4 oz. extra-sharp cheddar, preferably aged, chopped, and reserved eggs. Pour remaining maple vinaigrette over; season with pepper.