Cook the squash: Place over racks in the upper and lower thirds of your oven. Preheat the oven to 400 degrees F. Spread squash cubes in a single layer on a baking sheet, then drizzle with olive oil, salt, and pepper. Toss to coat. Bake the squash until tender and caramelized, 15-20 minutes, turning once throughout. Set aside.
Bake the bacon: Place an ovenproof baking rack on a second baking sheet. Coat with cooking spray, then arrange the bacon slices on the rack in a single layer. Place on the second rack in the oven with the squash. Bake until the bacon is as crisp as you like, about 12-20 minutes depending upon the thickness of your bacon. Transfer to a paper towel-lined plate and pat dry. Dice and set aside.
Hard boil the eggs: In a small pot, bring just enough water to cover the eggs to a gentle boil. Reduce the heat to a simmer and gently lower the eggs in with a slotted spoon. Bring water to a low, rumbling boil, then let cook for 9 minutes. A few minutes before the eggs are finished cooking, prepare an ice bath. Remove the eggs from the boiling water and plunge into the cold water. Let rest a few minutes, then tap the eggs with back of a spoon to crack them (this will make peeling easier). Return to the ice water to cool completely. Peel the eggs, then cut into slices. Set aside.
Make the dressing: In a small bowl or large measuring cup, whisk together the dressing ingredients: olive oil, apple cider vinegar, maple syrup, Dijon, garlic, salt, and pepper.
Place the salad greens in a large bowl. Add the butternut squash, bacon, chicken, eggs, and apple. Drizzle with the dressing, toss gently to coat. Scatter the avocado, cranberries, goat cheese, and pepitas over the top. Enjoy!
TO MAKE AHEAD: The butternut squash, bacon, eggs, and chicken can all be prepared 2 days in advance. The dressing can be prepared up to 5 days in advance. Store items individually in the refrigerator. When ready to serve, let the chicken, squash, and bacon come to room temperature, then assemble the salad as directed. If possible, wait to add the apple and avocado until right before serving, so that they don't turn brown.
TO STORE: Refrigerate leftover salad in an airtight storage container for up to 3 days.