Preheat the oven to 425 degrees Fahrenheit and line a rimmed baking sheet with parchment paper. Place the butternut squash on the pan and drizzle each half with just enough olive oil to lightly coat the squash on the inside (about ½ teaspoon each). Rub the oil over the inside of the squash and sprinkle it with salt and pepper.
Turn the squash face down and roast until it is tender and completely cooked through, about 40 to 50 minutes. Set the squash aside until it’s cool enough to handle.
Meanwhile, in a large soup pot, warm 1 tablespoon olive oil over medium heat until shimmering. Add the chopped shallot and salt. Cook, stirring often, until the shallot has softened and is starting to turn golden on the edges, about 3 to 4 minutes. Add the garlic and cook until fragrant, about 1 minute, stirring frequently. Transfer the contents to your stand blender.
Use a large spoon to scoop the butternut squash flesh into your blender. Discard the tough skin. Add the maple syrup, nutmeg and a few twists of freshly ground black pepper to the blender. Pour in 3 cups vegetable broth.
Securely fasten the lid. Blend on high until your soup is creamy.
If you would like to thin out your soup, stir in the remaining cup of broth. Add 1 to 2 tablespoons butter, to taste, and blend well. Taste and stir in more salt and pepper, if necessary.
Pour back into your soup pot and warm the soup over medium heat, stirring often, until it’s nice and steamy.
