Preheat the oven to 425°F and line a baking sheet with parchment paper.
Cut the acorn squash lengthwise into two pieces. Scoop out the seeds and discard.
Place the squash skin side down on the baking sheet and bake for 50 minutes, or until the fresh is tender with a fork.
In a skillet, add 1 tablespoon of extra virgin olive oil and heat on medium high heat. Add the ground turkey sausage and cook until browned, breaking it up with a wooden utensil.
Remove the cooked ground turkey from the pan and set aside on a plate.
In the same plan, add the second tablespoon of olive oil and add the chopped kale, garlic and red onion. Sauté for about 5 minutes or until the onions have softened.
Add the chopped apple pieces, dried cranberries and thyme. Cook for 1 minute more.
Turn off heat and stir in the cooked sausage.
Scoop the filling mixture evenly between the cooked acorn squash.
Place the baking sheet under the broiler for about 3 to 5 minutes. Season with salt and pepper before serving.