Coat a wide, straight-sided pan with olive oil and add the bacon. Bring the pan to a medium heat and let the bacon get brown and crispy.
Add the celery, onions and fennel and season with salt. Cook the veggies until they get soft and very aromatic, 8 to10 minutes. Add the rosemary and garlic and cook for 1 to 2 minutes more.
Toss in the chestnuts, cranberries and pears, and stir to combine. Add the wine and let it reduce by half.
Put the bread in a large mixing bowl and add the cooked veggie mixture to the bread. Stir to combine and douse the bread with half the stock. Use your hands to combine the bread, veggies and stock. Add more stock when/if needed to really saturate the bread. Season with salt and taste it to make sure it is delicious.
Use the stuffing to stuff a turkey or pork crown roast, or place in a roasting pan and bake for 35 minutes at 350 degrees F.