Preheat oven to 400 degrees F. Place the acorn squash on a baking sheet and roast for 45 minutes – 1 hour or until a fork can easily pierce the skin. Let cool slightly. Cut the squash in half and scoop out the seeds. Scoop out some of the flesh, leaving a "bowl" intact to fill later.
While the squash is roasting, prepare the farro stuffing. Combine 1 ½ cups farro with 4 ½ cups chicken broth in a medium saucepot. Bring to a boil over high heat. Cover, reduce heat to medium-low, and simmer until tender, about 20 minutes.
Melt 2 tablespoon butter in a large skillet over medium heat. Add the sausage and saute until browned, about 3-4 minutes. Add chopped onions, chopped apples, ¼ cup chopped celery, and 1 teaspoon minced garlic and saute until the vegetables have softened, about 5-6 minutes. Add 1 teaspoon Italian seasoning, ½ teaspoon oregano, ¼ cup dried cranberries, and ¼ cup white wine, and bring to a simmer. Cook until the wine has reduced by half.
Add the cooked farro, ¼ cup chopped parsley, ½ cup chopped pecans, and scooped out acorn squash, stirring to combine. Season the stuffing with salt and pepper.
Spoon the farro stuffing into the acorn squash and sprinkle breadcrumbs and grated parmesan. Bake the stuffed squash for about 7-8 minutes or until the cheese has melted and the breadcrumbs are toasted. Serve warm.