Preheat oven to 400 F. Cut acorn squash in half, then cut halves in half (you should come out with four quarters per squash and eight quarters total).
Brush squash with melted butter and brown sugar then sprinkle rosemary, sage, thyme, salt and pepper overtop. Bake in the oven for 30 min.
Meanwhile, make rice according to package directions in a rice cooker and chop up mushrooms. Mix together all ingredients for turkey sausage.
Heat olive oil in a large pan on med-high heat, then add turkey sausage mixture, breaking up into 1 inch pieces. Add shallots and garlic, sauteing for 3-4 min. Add mushrooms and saute another 3-4 min. Add beef broth, red wine and balsamic vinegar and simmer for 10 min until mushroom juices are mostly absorbed.
Add wild rice and parmesan cheese, cooking for another 2 min. Remove from heat and stir in sage, thyme, kale, salt and pepper.
Squash should be done cooking in the oven at this point so remove them and then stuff with the turkey sausage and rice mixture. There may be some leftover - you can freeze it to use for another time!
Bake squash with stuffing in the oven for 5 min, then serve!