PreparationFor chipotle crème fra‮che: Combine Port, wine, chilies, and tomato paste in heavy small saucepan. Simmer over medium heat until reduced to thick paste, stirring often, about 12 minutes. Transfer to small bowl; cool. Fold in crème fraîche. Cover and chill at least 1 hour and up to 1 week. For soup: Preheat oven to 350°F. Brush baking sheet with oil. Place squash halves, cut side down, on prepared sheet. Bake squash until very tender, about 1 hour. Scoop squash from skins. Measure 6 cups squash and transfer to large pot (reserve any remaining squash for another use). Add broth and chestnuts to pot. Bring to boil over high heat. Reduce heat to medium-low. Simmer soup uncovered until chestnuts are very tender, about 30 minutes. Mix maple syrup into soup. Puree soup in batches in blender until very smooth; return to same pot. Season with salt and pepper. (Can be made 1 day ahead. Refrigerate until cold, then cover and keep refrigerated.) Rewarm soup. Ladle into bowls. Top each serving with chipotle crème fraîche.
PreparationFor chipotle crème fra‮che: Combine Port, wine, chilies, and tomato paste in heavy small saucepan. Simmer over medium heat until reduced to thick paste, stirring often, about 12 minutes. Transfer to small bowl; cool. Fold in crème fraîche. Cover and chill at least 1 hour and up to 1 week. For soup: Preheat oven to 350°F. Brush baking sheet with oil. Place squash halves, cut side down, on prepared sheet. Bake squash until very tender, about 1 hour. Scoop squash from skins. Measure 6 cups squash and transfer to large pot (reserve any remaining squash for another use). Add broth and chestnuts to pot. Bring to boil over high heat. Reduce heat to medium-low. Simmer soup uncovered until chestnuts are very tender, about 30 minutes. Mix maple syrup into soup. Puree soup in batches in blender until very smooth; return to same pot. Season with salt and pepper. (Can be made 1 day ahead. Refrigerate until cold, then cover and keep refrigerated.) Rewarm soup. Ladle into bowls. Top each serving with chipotle crème fraîche.