Preheat your oven to 400°F (200°C) and line a large baking sheet with parchment paper.
Brush the flesh of the halved acorn squashes with 1/2 tablespoon of olive oil. Place them cut-side down on the prepared baking sheet and roast for 40 to 50 minutes, or until the skin is easily pierced with a fork and the flesh is tender.
Remove the squash from the oven and let it cool for 10 minutes. Use a large spoon to scoop the roasted flesh out of the skins into a bowl; discard the skins.
In a large Dutch oven or heavy-bottomed pot, heat the remaining 1.5 tablespoons of olive oil over medium heat. Add the diced onion and carrots, sautéing for 8 to 10 minutes until the onions are translucent and the carrots have softened.
Add the minced garlic to the pot and cook for 60 seconds until fragrant, being careful not to burn it.
Add the roasted squash flesh, vegetable broth, maple syrup, nutmeg, cayenne pepper, salt, black pepper, and thyme sprigs to the pot.
Bring the liquid to a gentle boil, then reduce the heat to low. Cover and simmer for 15 to 20 minutes to allow the flavors to fully integrate.
Remove and discard the thyme sprigs. Use an immersion blender to purée the soup until it reaches a velvety, smooth consistency. If using a standard blender, work in small batches and vent the lid to allow steam to escape.
Stir in the coconut cream and simmer for an additional 2 to 3 minutes on low heat until the soup is rich and heated through.
Ladle the soup into bowls and garnish with toasted pepitas and a small drizzle of maple syrup if desired. Serve immediately.