You will need maple syrup, yellow onion, cherry tomatoes, nutmeg, olive oil, pepper, salt, butternut squash, on-the-vine tomatoes, red pepper flakes, cream, chicken stock, garlic, and cinnamon.
Preheat the oven to 400F. On one prepared baking sheet, add the quartered large tomatoes, whole cherry tomatoes, quartered yellow onion, head of garlic trimmed at the top, ¼ cup of olive oil, ½ teaspoon of salt, ¼ teaspoon of black pepper, and red pepper flakes.
On the other lined sheet pan, add the cubed butternut squash, remaining olive oil, ½ teaspoon of salt, ¼ teaspoon of black pepper, maple syrup, cinnamon, and nutmeg.
Then add the heavy cream and chicken stock. Place the pot on the stovetop and bring to a simmer over medium heat. Then reduce to low heat, cover, and continue to simmer for 5-10 minutes
Remove the soup from the heat. Using an immersion blender or carefully pouring the mixture into a high speed blender, blend the vegetable mixture until smooth and luscious.