Slice each acorn squash in half, scoop out seeds, and place on foil-wrapped baking sheet. Bake for 45 minutes.
Meanwhile, in a medium sauce pan, add rice and vegetable broth. Bring to a boil and then lower to a simmer and cover and cook for 45 minutes until rice is tender.
As squash and rice cook, put a large skillet over medium heat, add olive oil and onion, and sauté until onion is translucent.
Add salt, pepper, and sausage, and break up with a wooden spoon, then cook until meat is no longer pink.
Add chopped kale on top of sausage and cover with a lid, then cook on low for a few minutes until kale is bright green and slightly wilted. Stir to combine.
Remove kale and sausage mixture from heat and sprinkle with raisins and cherries, then stir to combine.
Once rice is cooked, add to mixture and stir to combine.
Scoop mixture into each acorn squash half, then serve.