Preheat your grill on medium high for 10-15 minutes.
In a 10-inch skillet, cook the sausage on the grill’s side burner set to medium-high heat until cooked through, about 5-8 minutes.
Add the mushrooms, bell pepper, onion, and celery and cook until the vegetables become transparent, about 5 minutes.
Add the kale leaves and cook for another 2-3 minutes. Transfer the mixture to a large bowl.
Add the bread cubes, pine nuts, and parmesan cheese and stir to combine. Add ¼ cup up to ½ cup of chicken broth until the mixture is moistened to your preference.
Season with kosher salt and ground black pepper, and more to taste.
Brush the cut side of the squash with olive oil.
Wipe the grates of the grill with a paper towel moistened with grapeseed oil. Grill the squash cut side down for 5-10 minutes.
Turn off the heat on one side of the grill and move the squash to that side, flipping the squash cut side up, and stuff the insides of the squash halves with the sausage mixture.
Top each half with gouda cheese and roast for 25-30 minutes or until the squash is tender. Serve with more parmesan cheese if desired.