Cut acorn squash in half and remove seeds. Brush with a little olive oil, then place cut side down on a baking sheet and roast for 15-20 minutes or until just soft. Remove and set aside once cool.
Meanwhile, cook the bacon in a pan large pot or deep pan. Once cooked, remove and set aside on a paper towel lined plate to let cool.
In the same pan, sautee onion with herbs and a bit of salt and pepper (if not using bacon, use a little olive oil). When onions are soft, add in the diced carrots and cook until carrots are just softened. Add in the cooked wild rice, chestnuts, cranberries, cooked bacon (if using).
Add in the broth and kale and continue to stir until kale is wilted. If the mixture is dry, add a little more broth (you want a little bit of sauce but not too liquid-y).
Stuff the partially cooked squash with the wild rice filling. You'll have quite a bit extra, but you can serve it with the squash, or use in other dishes (it's great on salads). Bake for 10-15 more minutes, or until squash is at desired softness.