Preheat the oven to 400F. Then, wash the acorn squash, slice each in half from stem to end, and remove the seeds & stringy flesh inside. Add the squash halves to a baking tray covered with parchment paper and season by rubbing with olive oil, salt, & pepper. Then, flip upside down so the fleshy inside is facing down and add to the oven to bake for 40-45 minutes until cooked through. Once cooked, flip over and set aside to be filled.
Once the squash is in the oven, add the wild rice and vegetable broth to a small saucepan and stir together. Cover, turn on the heat, and bring to a boil. Once boiling, reduce the heat to a simmer and cook for 40-45 minutes until cooked through. Cooked wild rice will be chewy, but should be tender.
While the squash and wild rice are cooking, make the filling. Cut the shallots, garlic, mushrooms, apples, and kale before starting. Then, add 2 tablespoon olive oil to a large pan and heat over medium heat.
Once the oil is hot, add in the shallots & garlic and sauté for 3 minutes until beginning to brown and caramelize. Then, add in the chopped mushrooms, stir, and cook together for another 5 minutes until the mushrooms are beginning to brown and crisp.
Next, add the chopped kale, chopped apples, salt, and pepper. Stir and sauté with the other ingredients over low heat for another 2-3 minutes until the kale has wilted and the apples are slightly cooked.
Then, turn off the heat and add in the pepitas, dried cranberries, cooked wild rice, fresh thyme, and fresh sage. Mix together and season with additional salt & pepper to your liking.
Fill each cooked acorn squash half with the wild rice stuffing. Then, garnish with additional fresh sage & thyme and serve warm. Enjoy!