Preheat oven to 375 f. degrees. Carefully slice acorn squash into 1/2" rings. Clean of all seeds. Place rings on a parchment lined baking sheet and season with salt and pepper. Spray or brush each ring with olive oil. Set aside.
In a saute pan with about 1 tablespoon of olive oil begin to saute the chicken sausage. While that is cooking finely dice the peppers and shallot. Mince the garlic. Add to pan with fresh sage. Continue to saute until vegetables have softened and the chicken sausage is cooked through. Carefully add a splash of white wine and half of the stock. Bring to a slow simmer.
In a bowl combine the bread stuffing cubes with grated cheese. Pour the sausage mixture over and mix with a spoon. Cover the bowl for aprox. 5 minutes to soften the stuffing. Remove cover and mix again. If stuffing cubes are still hard gradually add a little more stock until a softer consistency is reached.
Spoon the stuffing into each ring. Do not over stuff and press down gently on the top. Place tray of squash into a preheated oven for aprox. 25 minutes or until the squash rings are softened.
*Cover the squash with foil if the tops start to get too brown*
Remove from oven, garnish and serve warm.