Preheat the oven to 400ºF and lightly oil a sheet pan. Remove the stem from a small pie pumpkin (sometimes called sugar pumpkins) and cut the pumpkin in quarters. Scrape out all the seeds and fibers from the pumpkin quarters. Brush the pumpkin flesh with a light coating of olive oil and then place the quarters, flesh side down, on the oiled sheet pan. Roast until a fork easily pierces the pumpkin pieces and the flesh is beginning to brown. Remove from oven and let cool at least 30 minutes.

Once pumpkin has cooled, remove the outer skin and discard. The skin should peel away easily at this point. Place the pumpkin flesh in a food processor or blender and blend until a smooth puree forms. You may need to add a few tablespoons of water for the pumpkin to form a smooth puree as some pumpkins are drier than others. Set pumpkin puree aside.

Add the remaining 2 Tablespoons of olive oil to a large pot or Dutch oven and heat over medium heat. Once oil is hot, add the diced onion and cook until softened, about 5 minutes. Add the garlic and continue to cook until fragrant, about 1 minute. Add 3 cups of the pumpkin puree to the pan along with the broth, salt, and spices.

Turn the heat down to low and let the soup simmer for about 30 minutes, to allow the flavors to blend. After 30 minutes, stir in the maple syrup or honey and blend the soup to make it very smooth and silky. To blend: you can use a stick blender directly in the pan, or transfer the soup to a blender or food processor to blend. If using a blender or food processor, make sure the lid is vented to allow steam to escape, but covered loosely with a towel to prevent hot soup from splattering. After blending, serve soup immediately, drizzled with a little cream and/or sprinkled with cinnamon, if desired.