Preheat oven to 400°F (200°C). Cut butternut squash in half lengthwise and scoop out the seeds. Drizzle with olive oil and roast for 30-40 minutes, or until tender.
In a large pot or Dutch oven, sauté onion and garlic in olive oil until softened.
Add roasted butternut squash to the pot. Pour in vegetable broth and bring to a boil.
Reduce heat and simmer for 15 minutes.
Using an immersion blender or regular blender, puree the soup until smooth and creamy.
Stir in heavy cream and season with salt and pepper to taste.
Simmer for an additional 5 minutes to heat through.
Serve hot, garnished with a drizzle of cream, a sprinkle of cinnamon, and roasted squash seeds.