Step 1: Preheat your oven to 400°F (200°C). Carefully slice each acorn squash in half lengthwise, from stem to base. Use a sturdy spoon or ice cream scoop to remove the seeds and stringy bits from the center of each half.
Step 2: Drizzle the cut sides of the squash with 1 tablespoon of olive oil. Season generously with salt and freshly ground black pepper. Place the squash halves cut-side down on a baking sheet. Roast for 30-35 minutes, or until the flesh is tender when pierced with a fork.
Step 3: While the squash roasts, prepare the filling. Heat the remaining 1 tablespoon of olive oil in a large skillet over medium-high heat. Add the Italian sausage, breaking it up with a spoon as it cooks. Cook for 8-10 minutes, or until thoroughly browned and crumbled. Drain any excess grease, leaving about 1 tablespoon in the pan.
Step 4: Add the chopped yellow onion and red bell pepper to the skillet with the sausage. Sauté for 5-7 minutes, or until the vegetables have softened. Stir in the minced garlic and cook for another minute until fragrant.
Step 5: Add the diced apple, dried cranberries, and chopped fresh sage to the skillet. Cook for 3-5 minutes, stirring occasionally, until the apple softens slightly and the flavors begin to meld.
Step 6: Stir in the cooked farro (or your chosen grain/breadcrumbs) and pour in the chicken broth. Bring the mixture to a simmer and cook for 2-3 minutes, allowing the liquid to be absorbed. Taste and adjust seasoning with salt and pepper as needed.
Step 7: Carefully remove the roasted acorn squash halves from the oven. Turn them cut-side up. Generously spoon the prepared filling into each squash cavity, mounding it slightly. Return the stuffed squash to the oven and bake for an additional 10-15 minutes, or until the filling is heated through and the tops are lightly golden.
Step 8: Let the stuffed acorn squash rest for a few minutes before serving. Garnish with fresh chopped parsley, if desired. Serve warm and enjoy one of the most delightful acorn squash recipes!