Preheat the oven to 400°F and line a cookie sheet with parchment paper or foil (if using foil, spray with non-stick spray).

Cut the acorn squash in half and scoop out the seeds (see tips), brush with olive oil and sprinkle with sugar, salt and pepper.

Place on the cookie sheet cut side up and bake for 20 minutes, then flip upside down and continue baking for another 25 minutes.

To make the soup: Place the butternut squash, sweet potato, and carrots, on a foil lined cookie sheet sprayed with nonstick cooking spray (or parchment paper), and place in the oven with the squash bowls for 20 minutes. 

Once the diced vegetable mixture is done cooking, heat the olive oil in a large soup pan, then add the onions and sauté for 4 minutes, stirring often. Then add the garlic and cook for another minute. 

Add the roasted vegetables, the broth, thyme, sage, bay leaves, cinnamon, salt and pepper. Bring to a simmer and cook for 20 minutes.

Add the coconut milk and cook for 5 more minutes. Remove from the burner and blend till smooth with an immersion blender. (If you do not have an immersion blender, add half the soup to the blender and blend till smooth. Pour into a large bowl. Purée the remainder of the soup and pour all the soup back into the pan.)

Remove the roasted acorn squash from the oven and fill with the hot soup. Serve the soup with kale chips, pomegranate arils, pumpkin seeds or a spoon of cream on top.