Roast the Squash & Aromatics: Preheat your oven to 400°F (200°C) and line a large baking sheet with parchment paper. Toss the cubed butternut squash, chopped apple, and diced onion with 2 tablespoons olive oil, kosher salt, and black pepper. Spread into a single layer and roast for 25 to 30 minutes, until tender and caramelized with golden edges.

Infuse Aromatics & Simmer: In a large Dutch oven or soup pot over medium heat, warm 1 tablespoon olive oil. Add the minced garlic and 4 chopped fresh sage leaves, sautéing for 1 minute until fragrant. Add the roasted squash, apple, onion, and pour in the 4 cups of vegetable broth. Bring to a gentle simmer for 5 minutes to let flavors meld.

Blend to Silky Perfection: Using an immersion hand blender (or transferring in careful batches to a high-speed blender), puree the soup until completely smooth, velvety, and luxurious.

Finish with Cream & Spices: Stir in the heavy cream, pure maple syrup, and freshly grated nutmeg. Taste and adjust seasoning with additional sea salt and cracked pepper if needed. Keep warm over low heat.

Crisp Sage Leaves: In a small skillet, heat 1 tablespoon olive oil over medium-high heat. Drop in remaining whole sage leaves and fry for 15 to 20 seconds until crisp and fragrant. Drain on paper towels.

Garnish & Serve Warm: Ladle the velvety soup into warm bowls. Swirl an extra tablespoon of cream over the top, sprinkle generously with crunchy toasted pepitas, and crown with crispy fried sage leaves. Serve with warm crusty sourdough bread.