To make the maple-cider vinaigrette, whisk together the vinegar, maple syrup, mustard, salt, and pepper. Gradually whisk in the oil until completely blended. Set aside.
Heat a large skillet over medium-high heat. Add the bacon and cook until brown and crispy, about 6-8 minutes. Transfer the bacon with a slotted spoon to a paper towel-lined plate, reserving the bacon drippings in the skillet.
Add the cubed butternut squash to the bacon drippings. Use a wooden or metal spoon to stir the squash pieces so they are all well coated with the bacon drippings. Sprinkle generously with salt and pepper. Cover and cook until tender, about 10-15 minutes.
To assemble the salad, place the romaine and arugula in a large bowl and top with arranged rows of bacon, squash, eggs, apple, pepitas, cranberries, and cheese.