Start by roasting your garlic. Pre-heat the oven to 375 degrees. Using a sharp knife, slice about ½-inch off the top of the head of garlic, so that all of the cloves are exposed. Remove any excess papery skin from the garlic, and place the head on a sheet of heavy-duty aluminum foil. Drizzle the exposed cloves with a tablespoon of olive oil. Wrap the foil around the garlic so that the entire head is loosely enclosed in a sealed packet. Transfer the garlic to the oven and roast for 45 minutes until the cloves are very soft.
While your garlic is roasting, get going on the soup. Heat a tablespoon of olive oil in a Dutch oven or large saucepan over medium heat. When hot, add the onion, carrot, and celery and cook for about 5 minutes until the vegetables have softened and the onions are translucent. Add the cinnamon, smoked paprika, cayenne pepper and cook for 1 minute. Add the butternut squash and sage and cook for 1 minute more. (The sage will smell badass.) Add the vegetable stock and bring to a boil. Lower to a simmer and cook for 25-30 minutes until the squash is very tender.
Squeeze the roasted garlic cloves from their skins into the soup and simmer for another 5 minutes.
Purée the soup using an immersion blender/regular blender/food processor. Return soup to the saucepan and season with salt and pepper to taste.
Heat a small pan over medium-high heat. When hot, add the pepitas and toast, for 2-3 minutes, shaking the pan regularly, until lightly browned and fragrant.
Ladle warm soup into bowls and top with toasted pepitas and crumbled goat cheese. Serve immediately.