Preheat oven 425°F. Using a sharpened kitchen knife, cut the acorn squash in half vertically starting at tip down to the stem. Scoop out the seeds and discard. Rub oil all over squash and salt and pepper the cut sides. Place cut side up on lined baking sheet and bake for 40 minutes or until fork tender. Remove from oven and allow to cool.
Toast the sourdough bread slices and then cube, set aside.
In a large skillet over medium-high heat and the oil, sausage meat and start to brown, 4 minutes. Add the onion, celery, herbs, red pepper flakes and salt to taste. Cook for another 6 minutes. Remove from skillet and add to large bowl to cool.
When sausage mixture is cool enough to handle add the bread, egg and chicken stock. Toss to coat evenly. Add the cranberries and pecans and mix.
Divide stuffing mixture evenly between each squash half and press down gently to mold in cavity. Drizzle with maple syrup and bake for another 15-20 minutes, and tops are golden brown and crispy.
Use thick slices of bread, about the thickness of two sandwich bread slices.
I used half (8 ounces) regular pork sausage. There's also the Spicy HOT version if you'd like a spicier stuffing.
Substitute 1/2 teaspoon of ground sage if fresh isn't available.