Preheat your oven to 425°F (220°C) and prepare a baking sheet lined with parchment paper. Position the butternut squash halves on the sheet, cut-side up. Drizzle each half with a small amount of olive oil (about ½ teaspoon) and rub it evenly over the flesh. Season with a pinch of salt and pepper, then place the squash cut-side down on the sheet. Roast for 40 to 50 minutes, or until tender and fully cooked. Let the squash cool for about 10 minutes once done.

In a large pot over medium heat, warm 1 tablespoon of olive oil until shimmering. Add the chopped shallot and sprinkle with 1 teaspoon of salt. Cook, stirring frequently, until the shallot becomes tender and starts to turn golden around the edges, roughly 3 to 4 minutes. Add the minced garlic and cook for another minute until aromatic, stirring constantly. Transfer this mixture to a blender.

Scoop the flesh from the cooled squash into the blender, discarding the skin. Add the maple syrup, a few cracks of black pepper, and the nutmeg. Pour in 3 cups of vegetable broth, being cautious not to exceed the blender's maximum fill line. Blend in batches if needed, then combine any remaining broth later.

Secure the blender lid and blend on high until the soup is velvety smooth. If your blender has a soup setting, use it for a faster result. For a slightly thinner consistency, add the remaining cup of broth and blend again. Introduce 1 to 2 tablespoons of butter or an extra splash of olive oil, blending until incorporated. Adjust the seasoning with additional salt and pepper to taste.

If the soup is sufficiently hot after blending, pour it directly into serving bowls. If not, transfer it back to the pot and warm over medium heat, stirring regularly until it reaches your desired temperature. Serve each bowl with a sprinkle of freshly ground black pepper on top for an extra touch.