Step 1
Preheat oven to 375 degrees F (190 degrees C).
Step 2
Combine squash sweet potatoes olive oil salt and pepper together in a bowl; toss to coat. Pour out onto a baking sheet.
Step 3
Bake in the preheated oven flipping the vegetables once until slightly caramelized and tender about 60 minutes.
Step 4
Place bacon in a large skillet and cook over medium-high heat turning occasionally until slightly crisp 7 to 10 minutes. Reserve 1 tablespoon bacon drippings. Drain the bacon slices on paper towels; crumble bacon.
Step 5
Heat bacon drippings and butter together in Dutch oven over medium heat. Saute onion and butter in hot butter mixture until onion is translucent 7 to 10 minutes.
Step 6
Pour the white wine into the pan and bring to a boil while scraping the browned bits of food off of the bottom of the pan with a wooden spoon. Cook until white wine is reduced by half 3 to 5 minutes.
Step 7
Stir roasted squash mixture into onion mixture; add stock and bring to a boil. Reduce heat to low and simmer until all vegetables are tender about 10 minutes.
Step 8
Pour vegetable mixture into a blender no more than half full. Cover and hold lid down; pulse a few times before leaving on to blend. Puree in batches until smooth. Return pureed soup to Dutch oven.
Step 9
Stir half-and-half into pureed soup; cook and stir over medium-low heat until soup is warmed through about 5 minutes. Stir nutmeg into soup; season with salt and pepper to taste. Ladle into bowls and top each with crumbled bacon.