1. To prepare squash: Preheat oven to 400 degrees. Carefully cut the squash lengthwise through the middle and place the halves flat side down on a nonstick or parchment lined baking sheet. Pour 2 cups water into the pan and place the pan in the center of the oven with the necks of the squash toward the back of the oven. Cook the squash for about 30-35 minutes, or until the middle of the neck is soft enough to indent. Once it has cooled enough to handle, remove the seeds, peel and cut into 1 inch pieces.
2. For the soup: Melt butter in a large saucepan over medium-high heat. Add the cooked squash, pears, ginger and 4 cups of the broth. The broth should cover the squash. Bring to a boil, stirring often.
3. Add salt and cayenne pepper. Remove from heat.
4. Carefully puree the soup directly in the saucepan with a stick blender, if available. otherwise, pour the soup into a sieve set over a large bowl and strain. Place the pulp from the sieve and some of the strained soup broth in a food processor. Puree the pulp and soup broth in batches until smooth. Return puree and soup broth to the saucepan.
5. Simmer over medium heat, stirring often, for 5 minutes. reduce heat to low, stir in 1 cup of the cream and adjust the seasoning to taste. Thin the soup with milk to desired consistency.