Prep the produce: Peel and cube the squash, chop the carrots, apple, and onion, and mince the garlic. Try to keep the squash and carrot pieces similar in size for even cooking.
Roast for flavor: Heat the oven to 400°F (200°C).
Toss squash and carrots with 1 tablespoon olive oil, a pinch of salt, and pepper. Spread on a large sheet pan. Roast 25–30 minutes, stirring once, until tender and lightly caramelized.
Sauté the aromatics: In a large pot, warm 1 tablespoon olive oil over medium heat.
Add onion and a pinch of salt. Cook 5–7 minutes until softened. Stir in garlic, thyme, cinnamon, and nutmeg.
Cook 30 seconds until fragrant.
Add the apple and liquids: Add the chopped apple, roasted vegetables, broth, and apple cider. Stir and bring to a gentle simmer. Cook 10–12 minutes to meld the flavors.
Blend until silky: Turn off the heat.
Use an immersion blender to puree the soup until smooth. If using a countertop blender, work in batches and vent the lid slightly to let steam escape. Blend carefully.
Adjust the texture: If the soup is too thick, add more broth or hot water a little at a time.
If it’s too thin, let it simmer uncovered for a few minutes to reduce.
Season to taste: Stir in maple syrup if you want a hint of sweetness. Add butter or a drizzle of olive oil for richness. Taste and adjust salt, pepper, and spices.
Serve and garnish: Ladle into bowls.
Add a swirl of yogurt, cream, or coconut milk if desired. Top with toasted pepitas or nuts for crunch.