Preheat an oven to 375 Cut the squash in half lengthwise and remove and discard the seeds Brush the squash inside and out with olive oil and season wiht salt and pepper Place the squash cut side down on a baking sheet Using a sharp knife prick the skin in several places Add enough water ot teh baking sheet to just cover the bottom Roas the squash until a sharp knife penetrates the flesh easily about 1 hour When the squash is cool enough to handle scoop the flesh into a food processor Working in batches puree until smooth Transfer squash puree to a large saucepan and add the 3 cups stock Bring to a boil over medium high heat stirring occassionally Add the chestnut puree and 1/2 cup cream and stir to comgine If the soup is too thick add more stock Season wiht salt and pepper, keep warm In a small bowl whisk together the reamining 1/2 cup cram and the brandy until frothy Season iwht salt and pepper Ladle the soup into warmed bowls and garnish each serving with a drizzle of the cream