Preheat oven to 425°F. Peel and dice butternut squash and carrots. Peel garlic cloves. Toss in a 13x9 baking dish with 3 tablespoons of the olive oil, plus salt & pepper. Bake until squash is soft and carrots can just be pierced with a fork; about 45 minutes.
While the squash and carrots are cooking, peel and dice the onion, apple, and chop the herbs.
About 15 minutes before the squash is done, heat the remaining 3 tablespoons of olive oil in a large pot over medium heat.
Add the onion and cook, stirring, until onion starts to become translucent, about 10 minutes. Add the apple and cook for 5 more minutes. Add the herbs, and cook for 1 more minute, or until herbs become fragrant.
Add the roasted squash and carrot, chicken stock, and bring to a boil.
Reduce heat to a gentle simmer, and cook for 20 minutes, stirring occasionally.
Add maple syrup and remove from heat. Taste and add more salt & pepper if needed.
Blend the soup in the pot using an immersion blender, or use a regular blender by blending the soup in batches until smooth.
Serve in bowls with a nice crusty bread for dipping. Optionally, drizzle some Greek yogurt or sour cream on top of soup.