Preheat oven o 400 degrees F. Line a baking sheet with parchment paper.

Cut the squash in half lengthwise and using a spoon scoop out and discard the seeds. Brush the cut side with olive oil and season liberally with salt and pepper. Place them cut side down on your baking sheet and cook until tender, roughly 25 minutes. Once cooked remove them from the oven, turn them over but keep them on the same baking sheet and set them aside. Keep your oven at 400 degrees F.

Heat a large pot over medium high heat. Once to temp add your sausage and cook thoroughly while breaking the sausage up into smaller pieces. Spoon out the sausage onto a plate and set aside. Add your unsalted butter to the same pot and cook until melted. Then add in your chopped onion and carrots and cook until slightly tender. Add your dried cranberries and continue to cook for another 5 minutes.

Once the carrots and onions are tender and the cranberries are soft add back in your sausage and your prepared long grain and wild rice and combine. Mix in your kale, sage and salt and pepper to taste.

Turn off the heat on your pot and let your sausage and rice mixture cool slightly. Then with a spoon, start stuffing your acorn squash with your filling mixture. Place the stuffed squash back into the 400 degree oven for another 20 minutes until the squash is fully tender and the stuffing is golden brown on top.

Remove from the oven and enjoy!