Preheat the oven to 400ºF.In a shallow baking dish, add 1/4 inch of water and place the two squash halved face down. Place in the center of the oven for 20 - 30 minutes.
While the squash is cooking, toss the cauliflower with 1 tablespoon olive oil and 1 tablespoon curry powder. Add salt and pepper to taste. Place on a baking sheet and roast in the oven for 20 - 25 minutes, turning halfway through.
On the stovetop, heat the remaining tablespoon of oil in a large saucepan (or dutch oven) and sauté the onions, carrots, parsnips and garlic together until the onions are translucent and the carrots have begun to soften. Add the cauliflower when it is done roasting, and sauté for another few minutes.
When the squash is done, scoop the flesh out of the skins and add it to the pot. Add the vegetable broth, water, coconut milk, salt, pepper and the remaining curry powder (add more of any if you'd like) and bring the soup to a boil. Turn it down to medium-low and let it simmer for another 10 - 15 minutes.
Take the soup off the heat and with an immersion blender, or in a high powered blender, puree it until it's smooth and creamy.
Serve hot and garnish with a touch of coconut milk (or yogurt) if you so choose. Enjoy and stay warm!
Store curried cauliflower and acorn squash soup in an airtight container in the fridge for up to four days.