Preheat the oven to 425 degrees. Line a being sheet with aluminum foil and set aside. Cut each squash in half, remove the seeds and place the squash on the baking sheet. Drizzle olive oil over the face of the squash and sprinkle with salt and pepper.
Roasted the squash for 45 minutes or until tender. Remove from the and allow it to cool until is easily handled. When the squash has cooled, scoop out the pulp and place in a blender along with the broth, blend until combined.
Pour the soup into the pot and season with salt, pepper (to taste) paprika, and garlic powder; stir. Heat until warm.
Garnish soup with crumbled up bacon and croutons.