Preheat oven to 375°F and spray a baking sheet with oil; spread squash onto sheet and spray again to lightly cover surface of squash. Roast for 20-30 minutes, until tender.
Place carrot, celery, garlic, potato and the chopped half of the onion in a large pot with 2 cups water, herbs, and salt; stew over medium-low heat to create stock, about 30 minutes.
Remove squash from oven and stock from heat (remove bay leaves) and allow to cool while preparing Topping.
Topping: Heat olive oil in a large skillet over medium heat. Add apple, bell pepper, and sliced half of the onion and sauté for 5 minutes; reduce heat to low and allow to caramelize, stirring occasionally, about 10 minutes. Set aside.
Combine 1/2 of cooled squash with stock, including vegetables, in a blender or food processor until smooth; pour into a large bowl as a holding place. Now blend remaining squash with coconut milk until smooth. (If there is not enough liquid to blend smoothly, add more water.) Then pour both mixtures back into the large pot. Stir well and simmer on low for 10-15 minutes.
To serve, pour into bowls and top with a spoonful of Apple-Onion Topping.