Preheat your oven to 400°F (200°C). Spread the cubed butternut squash and chopped carrots on a baking sheet, then drizzle with olive oil. Toss to coat evenly and roast for about 25-30 minutes until tender and caramelized around the edges.
Transfer the roasted vegetables to a large pot. Pour in the broth and bring the mixture to a gentle simmer over medium heat. Let it cook for about 5 minutes to meld the flavors.
Use an immersion blender or transfer the hot mixture to a blender, then blend until completely smooth and creamy. Be careful with the hot liquid during blending.
Stir in the maple syrup and season with salt and pepper to taste. Blend again briefly to combine all the flavors.
Return the soup to low heat if needed, and warm for a few minutes while stirring gently. The soup should be velvety, thick, and vibrant orange in color.
Serve the hot soup in bowls, garnished with a drizzle of olive oil or a sprinkle of herbs if desired. Enjoy the rich, sweet, and earthy flavors in each spoonful.