Adjust oven rack to middle position and heat oven to 400°F. Spray a large roasting pan with nonstick spray.
In a large bowl, whisk together olive oil, maple syrup, soy sauce, crushed red pepper flakes, allspice, 1 teaspoon salt, and ½ teaspoon black pepper.
¼ cup olive oil, 2 tablespoons maple syrup, 2 tablespoons low-sodium soy sauce, ¼ teaspoon crushed red pepper flakes, ⅛ teaspoon ground allspice, 1 tablespoon kosher salt, ¾ teaspoon freshly ground black pepper
Cut off both ends of the squash, peel it, and cut it in half from top to bottom. Scoop out and discard the seeds and strings (much like cleaning a pumpkin). Place the squash, cut side down, on a cutting board and cut into 2-inch thick pieces. Place the squash pieces in the bowl with the olive oil mixture.
1 large butternut squash
Peel and core the apple then cut into ½-inch slices. Add the slices to the squash/olive oil bowl.
1 Golden Delicious apple
Peel and halve the carrots top to bottom (the long way). Cut each section into thirds. Add to the vegetable/oil bowl.
½ pound carrots
Peel and quarter the shallots. Add them to the vegetable/oil bowl.
Cut the garlic head in half horizontally and add to the vegetable bowl.
1 head garlic
Toss the vegetables with the oil/syrup mixture and arrange the vegetables, in a single layer, onto the prepared roasting pan. Spread the vegetables out and place the garlic cut-side down. Drizzle remaining liquid over the vegetables and roast, at 400°F, for 30 minutes - stir halfway through roasting. If any vegetables can be easily pierced with a fork after 30 minutes, transfer them from the oven to a large bowl and set aside. Bake the remaining vegetables/fruit for another 15 minutes or until they are fragrant, have some color, and are knife tender.
Pour 2 cups of broth into the roasting pan and use a wooden spoon to deglaze (scrape up any browned bits). Stir and return the pan to the oven and roast until liquid has been reduced, about another 5 minutes. Remove the roasting pan from the oven and remove the garlic; set aside to cool a bit. Pour the remaining vegetables and any liquid into the bowl with the roasted vegetables.
6 cups chicken broth
Squeeze the cooked garlic from the peels and into the roasted vegetable bowl.
Working in 2 batches, purée the vegetables and remaining liquid in a blender until smooth.
Pour the puréed vegetables into a large Dutch oven, add the remaining chicken broth, star anise, and grated ginger and bring to a boil. Reduce the heat to a simmer, partially cover the pot and simmer 30 minutes. Season with more salt and black pepper, if needed.
1 star anise, 1 1-inch piece of fresh ginger
Remove the star anise.
The soup should be smooth, but if needed, it can be pureed in the blender (in batches). *Be careful when puréeing hot soup! It’s easy to burn yourself so be extremely careful.*
For serving: Drizzle with heavy cream and olive oil and top with homemade cinnamon croutons, if desired.
Olive oil for drizzling, Heavy cream for drizzling, Homemade cinnamon croutons or plain croutons for garnish