Preheat oven to 425F and line a baking sheet with parchment paper and set aside.
Pour olive oil over the acorn squash and sprinkle with salt and pepper.
Bake in over for 50-60 minutes, until skin is soft and fork-tender (Roasting time will vary depending on the size of your squash).
While squash roasts, heat 1 tablespoon olive oil in a skillet over medium-high heat.
Add sausage and using a wood spoon break into coarse pieces. Cook until brown. It’s about 5-6 minutes. Then, set it aside, but leaving fat in the skillet.
In the same skillet, add onions and green bell pepper; cook until they’re soft, 3-5 minutes. Add garlic and cook for 30 seconds.
Add diced apple, thyme and salt and pepper to taste. Cook for 1 minute and add chopped kale and cranberry. Cook for 2-3 minutes. Stir occasionally.
Bring back the sausage and stir well to combine and cook just for 1-2 minutes to blend flavours.
Preheat your broiler and divide apple-sausage filling among squashes.
Once filled, place the baking sheet under the broiler and broil until for 5 minutes or so. Garnish with fresh minced parsley and enjoy!