Roast the Vegetables & Garlic: Preheat your oven to 400°F (200°C) and line a large baking sheet with parchment paper. Arrange cubed butternut squash, chopped apple, and onion on the sheet. Drizzle with 2 tablespoons olive oil, kosher salt, and black pepper; toss evenly. Drizzle the exposed garlic head with remaining olive oil and wrap tightly in aluminum foil, placing it on the baking sheet. Roast for 30 to 35 minutes until the squash is caramelized and fork-tender.

Transfer to Dutch Oven: Transfer the hot roasted squash, apples, and onions into a large Dutch oven or soup pot over medium heat. Squeeze the soft, caramelized roasted garlic cloves out of their skins directly into the pot.

Simmer with Broth & Herbs: Pour in the vegetable broth, minced rosemary, fresh thyme, ground nutmeg, cinnamon, and pure maple syrup. Bring to a gentle boil, then reduce heat to low, cover, and simmer for 10 minutes to marry the rich autumn flavors.

Puree Until Silky Smooth: Use an immersion hand blender directly in the pot to puree the soup until completely smooth and velvety with zero lumps. (Alternatively, transfer in batches to a high-speed blender and blend until ultra-smooth).

Stir in Cream & Season: Pour in the heavy cream and stir over low heat until heated through. Taste and adjust seasoning with additional salt, black pepper, or a teaspoon of maple syrup if desired.

Garnish & Serve: Ladle hot soup into shallow ceramic bowls. Create an elegant circular swirl of heavy cream, top with crispy garlic sourdough croutons, roasted pepitas, fresh thyme, and freshly cracked black pepper. Serve warm with crusty sourdough bread!