Preheat the oven to 400° F.
Cut the large pumpkin into fourths, removing the seeds. Place on a baking sheet and rub 1 tablespoon olive oil and a sprinkle of salt and pepper.
Chop off the top portion of the garlic head to reveal the cloves. Drizzle with a teaspoon of olive oil and wrap with foil. Add to the baking sheet with the pumpkin.
Roast for 45 minutes, until the pumpkin is fork tender. Cool for 5-10 minutes.
Place pumpkin in a food processor and puree with 1 cup of the chicken broth, until completely smooth. See NOTE.
Heat a large pot over medium heat. Add butter and shallots and sauté until soft, about 5 minutes. Next, add the thyme and stir for another 30 seconds.
Add the pumpkin puree, roasted garlic (squeeze the cloves from the paper), remaining 3 cups chicken broth, coconut milk, water, cayenne, nutmeg, maple syrup, and crushed red pepper. Bring the soup to a low simmer and simmer 15-20 minutes.
To assemble the soup, ladle the soup into the roasted pumpkins and top each bowl with a sprinkle of pumpkin seeds and a drizzle of cream (or coconut milk).