Roast the squash: Slice the squash in half lengthwise (carefully, with a very sharp knife).
Remove the seeds and pulp from the bulb with a spoon, and brush the cut sides of the squash with olive oil.
Season the cut sides of the squash with salt and pepper, and place cut side down on a foil or parchment lined baking sheet.
Roast the squash for 45-55 minutes in a 375 degree oven, or until the flesh is easily pierced with a fork.
Flip cut side up to cool before adding the the soup.
Once cooled, scoop out the flesh, discard the skins, and set aside.
Heat olive oil over medium heat in a large soup pot or dutch oven.
Add onion, season with salt and pepper, and cook, stirring occasionally, until softened, 5 minutes.
Add the brown sugar, garlic and ginger, and cook, stirring occasionally for 2 minutes.
Add the broth, vinegar, and squash. Bring to a boil over high heat.
Once boiling, reduce heat to low, and simmer 5 minutes, stirring occasionally.
Add coconut milk and nutmeg. Simmer 2-3 minutes until warmed through.
Blend well with an immersion blender until smooth. (Alternatively, blend in batches in a traditional blender.)
Taste, add salt and pepper if needed, and serve hot!
Notes:
You can use an equal amount of frozen butternut squash cubes for this recipe as well, just be sure to simmer longer to cook them through.
You can roast the squash up to 3 days ahead of preparing the soup, and store it in the refrigerator!