Adjust oven rack to middle position and preheat the oven to 400°F. Toss squash, apples, shallots, garlic, oil, salt, and pepper in large bowl, then arrange in single layer in a large roasting pan. Roast, stirring every 10 minutes, until vegetables are golden brown and softened, about 40 minutes. Add ½ cup of the stock to the pan and scrape up any browned bits with a wooden spoon. Return to oven and cook until the liquid has reduced and the vegetables are glazed, about 5 more minutes.
Purée the squash mixture with the remaining broth in a blender until smooth. Transfer puréed squash mixture to a large saucepan and stir in the maple syrup, vinegar, nutmeg, and cream. Bring the soup to a simmer over medium-low heat, adding ¼ cup warm water at a time if necessary to adjust the thickness. Taste and adjust the seasoning.
Top the soup with a few crispy, sautéed sage leaves and sprinkle with some minced fresh chives. If you like the heat, you can also add a pinch of pepper flakes. Serve the soup warm. Leftovers can be refrigerated in an airtight container for 4 days.
Notes
When purchasing a butternut squash, choose one with a relatively long neck – those have more usable flesh and have less stringy fibers and seeds. To save time, you can purchase a butternut squash already peeled and cut in chunks.
Recipe by Marilena's Kitchen at https://marilenaskitchen.com/roasted-butternut-squash-soup/