This rich, creamy soup has real depth, with roasted squash, cinnamon-spiced cream and Parmesan simmered together until velvety-thick. Make it now, or freeze the roasted squash to cook later.
Preheat oven to 400 (200C) degrees. Line a baking sheet or baking pan with parchment paper.
Slice 1 3-4 pound butternut 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.
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
While the squash is roasting, pour 1 cup heavy cream into a small saucepan and add 3 whole garlic cloves and cinnamon stick. Bring just to a boil, then immediately remove from the heat and allow the flavors to steep 15-25 minutes.
Heat 2 tablespoons extra virgin olive oil in a Dutch oven over medium heat. Add 1 chopped yellow 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).
Add the cooked squash to the pot. Stir in 2½ cups of the broth, ¼ cup of the Parmesan, 1½ teaspoons salt and ½ teaspoon crushed 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.
Serve the soup in bowls, sprinkled with some parsley, chili and Parmesan cheese.
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Notes
Roast the squash up to 3 days in advance: Scoop out the flesh and store in a container or ziptop bag, or freeze up to one month.
To add more warm spicy flavor, add 1/4 teaspoon each of ground ginger or 1/8 teaspoon of nutmeg to the cream infusion.
Skipping the cream-infusion step? Cook 1–2 thinly sliced garlic cloves with the onion, add a dash of ground cinnamon, then stir the cream straight into the pot.
Butternut squash soup keeps in the refrigerator 3-5 days, and in the freezer for 1 month.
If you use a blender to puree the soup, be careful to only fill the blender jar about halfway. Hot soup expands quickly under pressure, making a mess if it explodes out of the lid.
If you happen to have a high-speed blender, you'll love how super-smooth and creamy this soup will turn out. But next to that, an immersion stick blender like this one does the trick almost as well — it's what I use most of the time.