Preheat oven to 375?F.
Place the squash on a flat surface and split them in half lengthwise. Scrape out the seeds and arrange in a single layer on one or two baking sheets.
In a small saucepan, melt 1 stick of the butter completely over medium heat. Wait until it starts to turn a light brown color. Remove from heat and immediately distribute the butter into the cavities of the squash halves. Sprinkle with the brown sugar and Molasses as well.
Season the insides with salt and pepper. Finish by covering with the ground (dry) ginger, fresh ginger, and the ground cloves. Fill the bottom of the tray(s) with the water (should be about 1 inch high) to create steam while the squash bakes in the oven. Cover the tray(s) with aluminum foil and seal the edges tightly.
Place the tray(s) in the center of the oven and bake, undisturbed, for 2 hours. To check for doneness, pierce one of the halves with the tip of a small knife. The knife should slide in and out easily. If at all firm, bake the halves an additional 30-45 minutes. Remove from the oven. Carefully peel back the foil. Set aside to cool.
Make the Soup: Using a large spoon, scoop the flesh from the squash, taking care not to take any skin with it. The skin can give a bitter flavor; however, take care to retain all of the cooking liquid inside the squash. That will add a lot of flavor to the soup. Gather all of the squash in a large pot. Turn the heat on low. Add half of the orange zest, the orange juice, the Worcestershire Sauce and the garlic. Stir to blend. Taste for seasoning. If the squash lacks sweetness, add a little Molasses. If it lacks salt, add a little salt or Worcestershire Sauce.
In a medium saucepan, heat the remaining 4 tablespoons of butter over medium heat until it turns light brown. Pour over the squash, stirring to blend. In the same pot, heat the milk, heavy cream, and two cups of the water. Season the liquid with salt and pepper and bring to a simmer.
Stir the milk mixture into the squash and stir to blend. Once the mixture has returned to a simmer, taste for seasoning.
Puree the soup in small batches in a blender. Combine all the batches and taste for seasoning. If the soup needs more flavor, add salt, extra orange zest or pepper, as needed. If the soup is too thick, add the additional cup of water and blend. Serve the soup family style or ladle the soup into individual bowls with popcorn on the side.