Place an oven rack on the center shelf and preheat the oven to 425°F.
Rub the insides of the squash with 1 tablespoon olive oil. Sprinkle with salt and pepper. Place skinside down on a large baking sheet and cook until tender and slightly brown around the edges, about 25 minutes.
While the squash is cooking, prepare the filling. Heat the remaining olive oil in a medium-sized skillet over medium heat. Add the onion, mushrooms and kale. Cook, stirring occasionally, until the vegetables are soft and the onions are starting to caramelize a bit, 5-7 minutes. Stir in the garlic and cook for an additional minute, then remove from the heat.
In a large bowl, combine the brown rice, dried cranberries, walnuts, cinnamon, and vegetable mixture. Season with salt and pepper to taste, if desired.
Once the delicata squash is cool enough to handle, carefully flip over so that they’re skin side up. Divide the filling between the squash, top evenly with parmesan cheese, and bake for an additional 7-10 minutes (until the cheese is melted).
Sprinkle with fresh parsley and serve.
Notes
Serves 2 as a main, or 4 as a side.
Cremini, white button, or shiitake mushrooms are all good options in this recipe.