Roast the Vegetables: Preheat oven to 400°F (200°C) and line a large baking sheet with parchment paper. Arrange cubed butternut squash, chopped onion, and apple pieces on the sheet. Drizzle with 2 tablespoons olive oil, sprinkle with salt and pepper, and toss to coat. Drizzle the exposed garlic head with 1 tablespoon olive oil and wrap snugly in aluminum foil. Place garlic cut-side up on the baking sheet.

Caramelize in the Oven: Roast for 35 to 40 minutes, tossing squash once halfway through, until fork-tender with golden-brown caramelized edges. Remove from oven and let cool slightly.

Simmer with Broth & Herbs: Transfer roasted squash, onion, and apple into a large Dutch oven or soup pot over medium heat. Squeeze the soft roasted garlic cloves out of their paper skins directly into the pot. Pour in the 4 cups vegetable broth, fresh thyme, sage, and nutmeg. Bring to a gentle simmer for 8 minutes to meld flavors.

Puree to Velvety Smoothness: Use an immersion hand blender directly in the pot (or transfer in batches to a high-speed countertop blender) and blend on high for 2 minutes until completely smooth, silky, and lump-free.

Stir in Cream & Adjust Seasoning: Reduce heat to low. Stir in heavy cream (or coconut milk) and pure maple syrup. Taste and season with additional sea salt and black pepper as needed. Simmer gently for 2 more minutes until piping hot.

Garnish & Serve: Ladle warm soup into deep bowls. Create a decorative swirl of heavy cream, drizzle with olive oil, scatter crunchy pepitas and fresh thyme leaves over the top, and serve with crusty sourdough bread!