Preheat the oven to 425 degrees F. Line a baking sheet with foil. Set aside.
Cut the acorn squash in half horizontally. (This gives the finished product a pretty shape.) Scoop out the seeds and lay the squash cut side up on the prepared baking sheet.
Brush the inside of the squash with olive oil. Sprinkle with garlic powder, salt, and pepper.
Roast for 25 to 30 minutes until tender. Carefully drizzle the squash with maple syrup, and then roast for another 5 minutes.
Filling
While the squash roasts, add the olive oil to a large skillet over medium heat. Once hot, add the onions and carrots and cook for 2 minutes. Stir in the garlic and cook for 30 seconds.
Push the veggies to the outside of the pan and add the sausage to the center. Break up the meat and season with the sage, salt, and pepper. Cook until the sausage is cooked through and no longer pink.
Stir in the pear and rice. Cook, stirring often, until everything is warmed through.
Remove the roasted squash from the oven. Fill each half of the squash with sausage mixture so they are overfilled. Place the baking sheet back in the oven for 5 minutes. Remove from the oven and serve warm.
Notes
Depending on the size of your squashes, there may be extra filling. This can be divided among the plates and served on the side of the squash, or saved for later and reheated to eat by itself.