Preheat oven to 400°F and position rack in the middle of the oven.
Place the squash (peeled and diced) on a sheet pan. Add 2 tablespoons of Bacon Up to the maple syrup, 1 teaspoon of salt and 1/2 teaspoon of pepper; toss. Roast the squash for 15 to 20 minutes, turning once, until tender. Add the cranberries to the pan for the last 5 minutes.
While the squash is roasting, combine the apple cider, vinegar and shallots in a small saucepan or skillet set over medium heat. Simmer until the mixture has reduced by half.
To a small bowl, add mustard and hot cider mixture; whisk to combine. While whisking, slowly stream in the Bacon Up and olive oil. Taste and adjust seasoning with salt and pepper.
To a large bowl add arugula, roasted squash mixture and walnuts. Top with enough vinaigrette to lightly coat the ingredients and toss gently. Taste and adjust seasoning with salt and pepper. Top with Parmigiano-Reggiano cheese.