Preheat oven to 425ºF. Line a large rimmed baking sheet with parchment paper.
Place the butternut squash, carrots, onion, apple, sweet potato and garlic on the roasting sheet. Drizzle with olive oil and season generously with kosher salt and pepper.
1 large butternut squash, 3 large carrots, 1 large onion, 1 large Granny Smith Apple, 1 medium sweet potato, 1 head of garlic, the top 1/3 cut off, 1/4 cup olive oil, kosher salt and pepper
Transfer the roasting pan with all the vegetables to the oven.
After 30 minutes of roasting, or as soon as they're soft and caramelized, remove the apple and head of garlic from the oven. I transfer them to another rimmed baking sheet on the counter. Then flip the carrots and sweet potato to roast evenly.
After 45 minutes of roasting, or as soon as they're soft and caramelized, remove the carrots and sweet potato from the oven.
After 60 minutes of roasting, or once they're soft and caramelized, remove the butternut squash and onion from the oven.
Prepare the veggies for the blender. To the blender add the whole roasted apples, the whole roasted carrots and then squeeze out the roasted garlic bulbs. If the outside layer of the onion has gotten charred, peel off the charred layer and add in the softened roasted onion. Use your fingers to peel off the skin from the sweet potato. Discard the skin, and transfer the sweet potato flesh to the blender. Use a spoon to scoop out all the butternut squash flesh, discarding the skins.
Add the chicken stock to your blender, on top of all the veggies. I like to start with 2 cups in the blender so it doesn't get too full.
4 cups chicken stock
Blend on medium speed for 60-90 seconds until completely pureed.
Transfer the soup to a dutch oven or soup pot on your stove. Slowly add in the remaining 2 cups of broth until you reach your desired consistency. Bring the soup to a simmer. Season to taste with kosher salt and black pepper.
Serve warm. I topped mine with microgreens. Also great topped with chopped chives.
Leftovers will keep in an airtight container refrigerated for at least 5 days, or frozen for at least 6 months.
See the Recipe Notes below for more tips, FAQ's and ingredient substitutions.