Family Style Food

Roast the butternut squash
0 Preheat oven to 400 (200C) degrees. Line a baking sheet or baking pan with parchment paper.
1 Slice the squash in half lengthwise and scoop out the seeds with a large spoon. Drizzle the flesh side of the squash with olive oil and season generously with salt and black pepper.
8 Place the squash halves cut-side down on the baking sheet. Cover with a sheet of aluminum foil and bake until the squash is tender when pierced with the tip of a knife, about 35-40 minutes depending on the size of the squash. Set aside until cool enough to handle. Scrape the flesh from the butternut squash halves with a spoon. You should have 4-5 cups of squash. At this point, you can refrigerate it in a covered container until you're ready to make the soup (up to 3 days in advance).
Make the soup
3 While the squash is roasting, pour the cream into a small saucepan and add the garlic and cinnamon stick. Bring just to a boil, then immediately remove from the heat and allow the flavors to steep 15-25 minutes. 
2 Heat the olive oil in a large pot over medium heat. Add the onion to the pot. Cook, stirring frequently, until it's softened and translucent, 3-5 minutes. Pour the cream through a mesh strainer set over the soup pot (or just fish out the garlic cloves and cinnamon stick with a spoon). 
4 Add the cooked squash to the pot. Stir in 2½ cups of the broth, ¼ cup of the Parmesan, 1½ teaspoons salt and the red pepper. Bring to a simmer and cook 10 minutes. Puree the soup directly in the pot using an immersion blender until very smooth (or blend in batches in a blender). Stir in more broth as needed if you prefer a thinner consistency.
5 Serve the soup in bowls, sprinkled with some parsley, chili and Parmesan cheese.