Preheat oven to 425.
Peel butternut squash and cut into ½ inch cubes.
Line a baking sheet with a piece of parchment paper.
Add the squash in a single layer.
Toss with the 1 tablespoon of oil, and a touch of salt.
Bake for about 30 minutes, opening the oven at the halfway point to give it a quick toss with some tongs.
While the squash is roasting in the oven, chop the apple, bacon, and onion, and set aside.
Get out a Dutch oven (or large cast iron skillet).
Turn heat to medium and add the butter to coat the Dutch oven/skillet well.
Add the onion and celery and cook for about 5 minutes, until they begin to soften.
Next, add the italian sausage, bacon, and the seasonings (salt, sage, thyme and rosemary).
Mash everything together making sure to break up the sausage.
Cook for about 3-4 minutes, until lightly browned.
Add the chopped apple, cranberries, and butternut squash, giving everything a nice toss.
Transfer the Dutch oven to the oven and bake for 30 minutes.
If using parmesan cheese, sprinkle on top to garnish!