Preheat your oven to 425, cut up heirloom tomatoes (removing the core) into wedges and slice off the butt of 2 heads of garlic, half your butternut squash and scoop out the seeds, cut your white onion into wedges (remove the outer skin). Lay out on sheet pans and drizzle with olive oil, season with salt and pepper. Roast for 25 minutes and then broil for 5 additional minutes or until there’s some golden brown on your veg.
While baking, make your pumpkin seed pesto by adding all of the pesto ingredients to a food processor and pulsing until it has reached your desired consistency. Should be liquidy but not pureed. Store in a jar and set aside.
Remove veggies from oven and let cool. To a large pot, add all of your veg (squeeze out the garlic cloves from their coats), and scoop out your butternut squash. Add in nutmeg, cinnamon, red pepper flakes, smoked paprika, and salt and mix well. Add in 1 cup of veggie broth and bring to a simmer to make sure your squash is soft enough to blend. Add in fresh basil. Simmer on LOW for 15 minutes with lid on.
While simmering, make your croutons by cutting slices of French bread into cubes. Toss with a generous amount of olive oil, season with garlic salt and ground sage and toss. Grate fresh parmesan and toss again. Bake at 425 for 15-20 minutes until golden brown and crispy. Do not flip or toss while baking.
Immersion blend (or transfer to blender) your soup contents until smooth. Add in 1/4 cup heavy cream and taste for any more additions (salt, cream, spices, etc.)
Serve your soup with pumpkin pesto and croutons and grate some more fresh parmesan on top! Enjoy!