Remove the stems, slice them into quarters (or eighths), and remove the innards and seeds. Reserve the seeds, if desired. Peel the pumpkin and chop up the pumpkin flesh. The yield of fresh pumpkin is about 12 cups, or 3 pounds in weight of peeled pumpkin. It's OK if you're off a little. Set them aside for now.
Add ½ cup peanut oil to a large pot and heat to medium heat. Add flour and stir. Cook for 10-15 minutes, constantly stirring, until the roux turns a light blonde brown. You can cook it longer for a darker, richer color and flavor.
Add pumpkin, peppers, onion, celery and garlic. Stir and cook about 5 minutes.
Add Cajun seasoning and chicken stock. Scrape up the brown bits from the bottom.
Cook at medium-low heat for 30 minutes to thicken. You can simmer longer if you’d like. I often simmer for 1 hour.
Process the mixture with an immersion blender, or transfer the soup in batches to a blender or food processor. Process until smooth.
Stir in the heavy cream.
Serve into bowls and garnish with fresh chopped herbs, spicy chili flakes and a swirl of extra virgin olive oil.