Preheat oven to 425°F (220°C). Place the cubed butternut squash on a large rimmed baking sheet. Drizzle with 2 tablespoons olive oil and toss with kosher salt and black pepper. Spread into a single layer and roast for 20 to 22 minutes, turning once, until fork-tender and deeply caramelized around the edges.

While the squash roasts, melt butter in a large enameled Dutch oven or soup pot over medium heat. Add the sliced shallots and diced apple. Sauté for 4 to 5 minutes until softened and fragrant. Add the minced garlic and cook for 1 minute until aromatic.

Add the roasted caramelized squash to the pot. Pour in the vegetable broth, maple syrup, ground nutmeg, and ground ginger. Bring to a gentle boil, then lower the heat and simmer uncovered for 5 minutes to allow the flavors to meld.

Remove pot from heat. Using an immersion hand blender directly in the pot (or working in batches in a high-speed blender), puree the soup on high speed for 2 to 3 minutes until completely velvety, silky, and lump-free. Stir in the heavy cream.

Ladle warm soup into shallow bowls. Drizzle with a swirl of heavy cream and olive oil, top with crispy fried sage leaves and toasted pepitas, and finish with cracked black pepper. Serve with warm crusty sourdough bread.