Preheat your oven to 400°F (200°C). Place the cubed butternut squash, chopped apple, yellow onion, and garlic cloves onto a large rimmed sheet pan. Drizzle with 2 tablespoons olive oil, sprinkle with sea salt, black pepper, nutmeg, and cinnamon, and toss to coat thoroughly. Spread in an even single layer. Roast for 30 to 35 minutes until the squash is fork-tender and the edges are beautifully caramelized.

While the vegetables roast, heat 1 tablespoon butter and 1 tablespoon olive oil in a small skillet over medium heat. Add the fresh sage leaves in a single layer and fry for 45 to 60 seconds until fragrant and crisp. Transfer immediately with a slotted spoon to a paper towel-lined plate. Reserve the sage-infused butter for drizzling over bowls.

Transfer the roasted squash, apple, onion, and garlic into a high-powered blender (or large Dutch oven if using an immersion blender). Pour in the vegetable broth and pure maple syrup. Blend on high speed for 90 seconds until completely velvety, creamy, and completely smooth.

Pour the smooth soup into a large pot over medium-low heat. Stir in the heavy cream (or coconut milk) and gently heat for 3 to 5 minutes until steaming. Taste and adjust seasoning with additional sea salt or black pepper if needed.

Ladle the hot velvety soup into warm shallow bowls. Swirl an extra splash of heavy cream over the surface, scatter with roasted pepitas, crown with crispy fried sage leaves, and drizzle lightly with the reserved sage butter. Serve immediately with warm crusty artisan bread.