Preheat oven to 425°F.
On a baking sheet, add butternut squash, cut head of garlic, shallot, and herbs. Season generously with salt, freshly cracked pepper and olive oil. Place baking sheet on the middle rack of oven. Roast for 40-50 minutes or until butternut squash is soft.
Set garlic aside and add the rest of the vegetables into a blender. When cool enough to handle, squeeze head of garlic so that roasted garlic falls into the blender. Discard papery leaves.
Add maple syrup, nutmeg, and 3¼ cups vegetable broth. Blend until smooth. Pour pureed soup into a medium saucepan and bring to a low boil over medium heat. Lower heat to a simmer and adjust seasoning with salt and pepper. Add more vegetable broth to thin out the soup, if necessary. Pour soup into bowls, garnish with more black pepper and serve.