Preheat oven to 400°F (205°C). Line a large rimmed baking sheet with parchment paper. Spread cubed butternut squash and quartered shallots across the sheet. Drizzle with 1.5 tablespoons olive oil, sea salt, and black pepper, tossing to coat evenly.

Drizzle remaining 1/2 tablespoon olive oil over the cut side of the garlic head, wrap tightly in a small piece of foil, and place cut-side down on the sheet pan. Roast for 25 to 30 minutes, tossing squash once halfway through, until fork-tender with golden caramelized edges.

Transfer roasted butternut squash and shallots into a large enameled Dutch oven or soup pot over medium heat. Carefully unwrap the roasted garlic and squeeze the soft, caramelized cloves directly out of their skins into the pot.

Pour in the broth, minced sage, fresh thyme, maple syrup, and ground nutmeg. Bring to a gentle boil, then reduce heat to low and simmer uncovered for 8 to 10 minutes to allow the roasted flavors and herbs to meld together.

Remove pot from heat. Using an immersion blender directly in the pot, puree on high speed for 2 minutes until completely smooth and velvety without any remaining chunks. (Alternatively, blend in batches in a heat-safe high-speed blender, venting the lid).

Stir in the coconut cream or heavy cream until fully incorporated. Taste and adjust seasoning with an extra pinch of sea salt or black pepper if desired. Warm over low heat for 2 minutes.

Ladle hot soup into shallow ceramic bowls. Drizzle a decorative spiral of extra cream over the surface. Garnish generously with crunchy roasted pepitas, a pinch of crushed red pepper flakes, and a crisp fried sage leaf. Serve immediately with warm artisan crusty bread.