1. Heat a large saucepan over medium-high heat. Add the bacon and cook until crisp, 5 to 6 minutes. Stir in the leeks and cook until they start to soften, 2 to 3 minutes. Add the squash, sweet potatoes, half of the pears, the carrots, and thyme; cook, stirring occasionally, until the vegetables are slightly softened, about 9 to 10 minutes. Stir in the nutmeg and cook for 30 seconds. Pour in the broth; bring to a boil, reduce the heat to medium-low, cover, and simmer until the vegetables are tender, about 30 minutes. Remove the saucepan from the stove and cool for 10 minutes.
2. Transfer the soup, in batches, to a blender and puree. Return the soup to the saucepan over medium heat. Stir in the cream, salt, and pepper and heat until hot, 1 to 2 minutes. Divide the soup among 8 bowls and garnish each with some of the remaining pear.