1. Preheat the oven to 425ºF. Line a rimmed baking sheet with parchment paper.
2. Cut or break garlic head in half. Cut the top from the head of garlic, leave root in tact. Drizzle olive oil onto the cut garlic cloves and salt lightly. Wrap in aluminum foil and set aside.
3. Cut the root and outer skin from the shallot, drizzle with a touch of olive oil. Wrap in aluminum foil and set aside.
4. Cut the squash horizontally, use a spoon to remove the seeds. Clean seeds, add to a piece of aluminum foil, drizzle with a touch of olive oil, salt lightly and close the foil packet.
5. Rub olive oil onto the inside of the squash. Add salt and pepper. Turn the squash cut-side down onto the parchment lined baking sheet.
6. Add foil-wrapped shallot, garlic and seeds to the parchment paper alongside the squash.
7. Roast squash seeds and shallot 20 to 25 minutes or until toasty and fragrant. Remove from oven and set aside.
NOTE: Check squash seeds. If they are still wet, unwrap foil and spread onto parchment for 5 to 7 minutes.
8. Continue cooking garlic for 15 to 20 minutes (40 minutes total cook time). Check squash and roast another 5 to 10 minutes (45 to 50 minutes total cook time) until browned and tender.
9. When cooled, scoop half the roasted butternut squash into the blender jar. Discard the outer skin. Replace yellow with the below.
10. Once cooled, add the cooked shallot. Remove the roasted garlic from its skin and add it to the blender jar. Add maple syrup, cinnamon, nutmeg and pepper.
11. Add the blender lid and blend on LOW. Once the mixture has been blended for a short time, remove the measuring cap and slowly add vegetable broth through the lid. The liquid should be added gradually while continuing to monitor the mixture. Add broth until the mixture has reached the jar’s MAX fill line. Secure the measuring cap back on the lid once the step is complete.
12. PULSE to combine ingredients. PUREE soup until creamy and smooth. Empty the mixture into a 3 qt. cooking pot.
13. Add the remaining half squash to the jar and repeat step 11.
14. When the desired consistency is achieved, add the last of the blended soup to the cooking pot and stir to mix. Reserve any leftover vegetable stock for future.
15. Warm soup before serving. Whisk plain Greek yogurt or sour cream with a splash of milk until creamy. Add a dollop to the soup. Garnish with toasted squash seeds.