Preheat the oven to 350F.
Halve the acorn squash and remove the seeds. Place the two halves back together and wrap the entire thing in foil. Bake for one hour until the squash is soft and cooked through.
While the squash is cooking, remove the casing from the raw chicken sausage. To a medium saucepan over medium-high heat, add the oil and the sausage and cook until no longer pink, using a wooden spoon to break up the sausage. Remove from the pan. Add the kale and give it a quick sauté until softened. Set aside..
Once the squash has cooked and cooled about 30 minutes, carefully remove the pulp from the squash, reserving the outside shell/skin and put into a medium bowl. Add the kale, sausage, salt, pepper, crushed red pepper and parsley. Mix all the ingredients together until well combined.
Preheat the broiler.
Divide the squash mixture up in between the two squash halves. Top each with half of the breadcrumbs and half of the cheese.
Place each squash half, cheese side up, on a baking sheet or baking pan. Broil until the top has charred slightly, about 5 minutes. Serve warm and enjoy!