Preheat oven to 400 degrees Farenheit. Slice squash in half lengthwise, remove the seeds, and place onto a baking sheet open side down. Bake for 25-40 minutes until it becomes browned and has a bubbly skin. Pierce with a fork to check for tenderness.
When soft, remove from oven and allow to cool. Remove the insides and toss into a blender along with remaining ingredients; puree until smooth.
Pour into a pot and heat over medium until slightly bubbly. If a thinner consistency is desired, add more water or coconut milk.
Top each bowl of soup with a drizzle of melted coconut oil and fresh pepper if desired. Serve with chilled grapes and wheat crackers on the side.