Cut the loaf of bread into 1-inch cubes. Place on a sheet pan. The bread can be left on the counter to dry overnight. You can also place it in a 350° oven for about 20 minutes to dry. Toss the bread after about 10 minutes so that all pieces are exposed to the heat of the oven and put back in the oven for another 10 minutes. You should have approximately 10 cups of dried bread cubes.
While the bread is drying, over medium-high heat, add 2 tablespoons of olive oil to a large saute pan. Once hot, add the diced onion. Season with salt. Saute the onions while occasionally stirring. The onions will start to release some liquid. When the onions start to get very soft and stick to the pan you should see a brown, crusty residue, better known as fond, start to develop on the bottom of the pan.
Add ¼ cup of the water to the pan and stir to deglaze. The fond will release as you stir the onions. Cook until the water is absorbed and the onions start to stick to the bottom of the pan again. Add another ¼ cup of water and repeat as above. Continue this process until the onions are a deep, rich color of brown.
Finish saute of ingredients
Take the onions out of the skillet. Add the pork sausage and break into small pieces, cooking for 5-7 minutes. Make sure the sausage browns nicely. This step adds a lot of flavor to the stuffing. While the sausage is cooking, peel and dice the pear.
Add the celery and stir to incorporate with the sausage. Saute for another 4 minutes. At this point add the onions back to the pan with the dried cherries and the diced pears. Pour the brandy into the pan and give everything a good stir. Deglaze the bottom of the pan, making sure to get all the brown bits on the bottom of the pan. Continue to cook until the brandy has been reduced. Turn off the heat and add the stick of butter to melt. Make sure everything is combined.
Assemble the stuffing
You will need a large bowl. Add the bread, the sauteed ingredients, and the herbs. Stir everything together. Add 2 cups of the chicken stock and again stir the ingredients. Season with salt and pepper. You will need a fair amount of seasoning, especially pepper. Pour in the last 2 cups of stock. Four cups of stock may seem like a lot. But take my word for it - the bread will absorb it all.
Coat the baking dish with cooking spray or vegetable oil. Place the stuffing in the pan making sure to not press down and compress the bread. Put in a 350° oven. Bake for 45 minutes until golden brown.
Use your favorite type of bread, making sure it is a sturdy type. French, Italian, or sourdough would be great choices. I used breakfast sausage because that is what my family likes. Italian sausage, mild or spicy, would also taste great.