Preheat oven to 400 degrees. Place squash on a sheet pan.Add 2 tablespoons olive oil the maple syrup, 1 teaspoon salt and 1/2 teaspoon pepper and toss. Roast the squash for 15 minutes until tender. Add the cranberries for the last 5 minutes. While the squash is roasting, combine the apple cider, vinegar and shallots in a small saucepan. Bring to boil over a medium heat. and cook for 6 to 8 minutes until the cider is about 1/4 cup. Off the heat, whisk in the mustard, 1/2 cup olive oil, salt and pepper. Place the arugula in a large salad bowl and add the Parmesan, squash, cranberries and dressing. Toss and enjoy!