Saute sausage in a large skillet over medium-high heat until cooked through, crumbling sausage with the back of a spoon, about 10 minutes.
Preheat oven to 350 degrees F.
Transfer sausage with a slotted spoon to a large bowl. Discard sausage fat in pan. Add butter, onions, and celery to skillet and saute until tender, about 10 to15 minutes. Add to sausage, along with herbs and croutons, mix to combine.
In a medium bowl, combine allspice, maple syrup, cherries, pecans, and chicken stock. Add to crouton mixture. The mixture should be moist, but not soggy. Add more chicken stock, if necessary. Transfer stuffing to a baking dish and cover with foil. Bake for 1 hour. Uncover and bake for another 20 minutes, or until the top is golden.