Start by preheating your oven to 375°F (190°C). Carefully cut each squash in half lengthwise and scoop out the seeds with a spoon. Brush the inside of each squash half with olive oil and sprinkle with salt and pepper. Place them cut-side down on a baking sheet and roast for about 30-35 minutes. You’ll know they’re ready when the flesh is fork-tender.

While the squash is roasting, grab your large skillet and cook the ground sausage over medium heat until browned and crumbly. Take it out of the skillet and set it aside. Using the same skillet, sauté the onion in a bit of olive oil until soft. Add minced garlic and stir for a minute to release its aroma. Toss in the diced apples and let them soften for a few minutes. Then, mix in the cooked sausage, cranberries, pecans, and sage. Sprinkle with salt and pepper, then give everything a good stir.

Once the squash is roasted, flip them over so the cut side is facing up. Generously stuff each half with the sausage and apple mixture. Return the squash to the oven and bake for another 15-20 minutes, allowing the filling to get lightly browned and warm throughout.

While the stuffed squash is baking, prepare the glaze. Melt the butter in a small saucepan over low heat, then stir in the maple syrup and cinnamon until smooth. Remove from heat.

Take the squash out of the oven and drizzle that warm, buttery maple glaze over each one. Serve hot and get ready to take in all the compliments!