Preheat the oven to 400F and line a baking sheet with parchment paper.
Cut the squash vertically and remove the seeds with a spoon.
Rub 1 tbsp of olive oil over the inside of the squash and sprinkle with salt and pepper.
Place the squash, face down on the parchment lined baking sheet.
Roast in the oven for 30-35 minutes, until the inside is golden and soft.
Meanwhile, chop the garlic and onion.
After the squash has been baking for about 15 minutes, sauté the onion and garlic in 1 tbsp of olive oil on medium heat in a large pot until translucent, about 7-9 minutes.
Once the squash is roasted scoop the squash out from the skin with a large spoon.
Add the squash to the pot.
Add the maple syrup, cinnamon, water and coconut milk into the pot.
Season with salt and pepper to taste.
Let the pot simmer for about 15 minutes to let the flavours develop.
After simmering for 15 minutes, blend the soup to smoothen it. Either carefully transfer the soup to a blender or use an immersion blender if you have one on hand.
If your soup is still hot after blending, you can pour it into bowls and serve. If not, pour the soup back into your pot and warm over medium/low heat, stirring often. Once the soup is hot, you are ready to serve!