Preheat your oven to 375°F (190°C). Cut the acorn squash in half lengthwise and scoop out the seeds. Brush the squash with olive oil, sprinkle with salt and pepper, and place them cut-side down on a baking sheet. Roast them for about 30-35 minutes, or until the flesh is tender when pierced with a fork.

Heat a large skillet over medium heat and cook the ground sausage until crumbly and browned. Remove it from the pan and set it aside. Using the same skillet, sauté the chopped onion in olive oil until soft and translucent. Add garlic and cook for another minute. Toss in the apples, letting them soften slightly. Return the cooked sausage to the skillet and stir in dried cranberries, pecans, and sage. Season with salt and pepper, then mix everything thoroughly.

Flip the roasted squash halves over so they’re cut-side up. Scoop the flavorful sausage-and-apple filling into each half generously. Place them back in the oven and bake for another 15-20 minutes, allowing the filling to brown slightly on top.

While the stuffed squash is in the oven, melt butter in a small saucepan over low heat. Stir in maple syrup and cinnamon until smooth. Remove from heat.

Once the squash is done, drizzle the warm maple glaze over the tops. Serve immediately and watch everyone devour this incredible dish!