Preheat the oven to 425° F.
On the baking sheet, toss together the butter, butternut squash, onion, sage, thyme, salt, and pepper. Add the garlic cloves. Bake for 20-25 minutes, until the squash is tender and the garlic is golden.
Meanwhile, in a soup pot, cook the bacon until crispy, then remove and set aside for topping.
When ready, add the roasted butternut squash, onions, garlic, herbs, and any butter left on the sheet pan to a food processor/blender. Puree until smooth. Pour the puree into the pot used for the bacon.
Set the pot over medium heat. Add the broth, chipotle, paprika, nutmeg and maple. Bring to a simmer, then add cream and pesto. Toss the cheese with cornstarch, then add to the soup. Simmer until melty.
Ladle the soup into bowls. Add a swirl of cream or shreds of cheddar. Then top with bacon and sage. And done! Enjoy!