1. Preheat oven to 400 degrees Fahrenheit.
2. Peel away most of the loose papery outer layers of the garlic, while still leaving the whole head intact. Trim about a quarter inch off the top of the head of garlic to expose the cloves. Drizzle with one to two teaspoons olive oil. Wrap the garlic in aluminum foil and bake for 40 minutes. Some heads might need an extra 10 minutes or so, depending on their size.
3. While the garlic is roasting, prepare the soup. Heat remaining olive oil up in a large pot over medium heat. Add in the diced onion and cook until translucent, about five minutes. Add in the butternut squash and broth.
4. Bring the soup to a boil, then lower to a simmer. Cover and cook for 35–40 minutes, or until the squash is very soft. When the garlic is ready, remove it from the oven and set aside to cool for a few minutes. When it’s cool enough to handle, squeeze the roasted cloves into the pot.
5. Blend and season to taste with salt and pepper. Add in the maple syrup and enjoy with croutons!