Preheat oven to 350 f (180 c)
Put squash, onion, apple, garlic cloves onto roasting pan. Sprinkle with cinnamon, nutmeg, a generals dosing of salt and pepper.
Roast in oven until vegetables are cooked and soft. Approximately 30 minutes)
Once cool enough to handle, remove squash from skin and squeeze out garlic.
Add everything to a soup pot with 6 cups of chicken broth. Simmer for 15 minutes.
Puree in blender or with stick blender. Add brown sugar to taste. Add more broth if needed to thin soup and reheat.
Heat 2-3 Tbsps olive oil in frying pan over medium high heat.
Add sage leaves and fry until crispy but not darkened. Remove and drain on paper towel.
Add bacon batons to pan and fry until golden brown and starting to get crispy. Add pumpkin seeds and cook another minute or two.
Add brown sugar and continue to stir until brown sugar has melted and caramelized over bacon and seeds.
Serve soup in bowls and top with a tablespoon of bacon and pumpkin seed mixture, and one or two fried sage leaves.