Start by slicing the acorn squash in half lengthwise. Scoop out the seeds with a spoon, creating a neat cavity for your stuffing. Give each half a generous brush of olive oil and sprinkle with salt and pepper. Pre-roasting the squash enhances its flavor and creates a tender texture, perfect for holding the filling.

Place the squash halves cut-side up on a baking sheet. Pop them into a preheated oven at 400°F (200°C). Roast for 30 to 40 minutes until the flesh is soft and golden around the edges. This step makes the squash easier to eat and more flavorful for the final dish.

While the squash roasts, heat a skillet over medium heat. Cook the sweet Italian sausage, breaking it into small crumbles with a spoon or spatula. Once fully browned and cooked through, transfer it to a plate lined with paper towels to drain excess grease.

Using the same skillet, sauté diced onions until translucent. Add minced garlic, followed by diced apples and fresh sage. Stir everything together and cook until the apples soften slightly. The aroma at this stage is just heavenly.

Combine the cooked sausage, sautéed apple mixture, and dried cranberries in a mixing bowl. Drizzle with maple syrup and gently mix until all the ingredients are well-blended. The filling should smell sweet, savory, and utterly irresistible!

Generously fill each roasted squash half with the prepared stuffing, packing it in as much as you can. Place them back onto the baking sheet and return to the oven for 15 to 20 minutes. This final bake deepens the flavors and brings a golden touch to the tops.