In a heavy-bottomed stock pot or Dutch oven, heat the olive oil over medium heat. Add the onions, garlic, oregano, and a pinch of salt. Cook, stirring occasionally, until the mixture is light golden brown, 6 to 8 minutes. Stir in the tomato paste and cook, stirring constantly to ensure it does not burn, until darkened, 2 to 3 minutes.
Stir in 4 cups of the vegetable broth, the tomatoes, and the pumpkin purée. Increase the heat to high and bring the mixture to a boil, using a potato masher or spoon to break up the tomatoes a bit. Once boiling, reduce the heat to medium-low, cover with a lid, and simmer for 15 minutes.
Take the soup off the heat and carefully purée the mixture until smooth using an immersion blender. For an even smoother texture, pass the blended soup through a fine-mesh strainer. Or, for a more rustic, chunky texture, you can skip blending. I love eating it chunky, but my family doesn’t, so I save a small portion in a bowl for myself before puréeing the rest of the soup for them.
If you like your soup thinner, add up to 1 more cup of vegetable broth or water and reheat the soup on the stovetop until warmed through. My family prefers this soup thicker, so we find that 4 cups of broth is perfect. Add the cream, salt, and pepper. Taste and adjust the seasoning if needed. Serve with a sprinkle of parsley, if using, and a drizzle of olive oil over each bowl. Leftovers can be stored in airtight containers in the fridge for up to 1 week or in the freezer for up to 1 month. When ready to eat, thaw the soup if frozen, spoon it into a bowl, and pop in the microwave for 45 seconds to 1 minute or until hot. Love the recipe? Leave us stars and a comment below!