Preheat oven to 375°F.
Cut the tops off the small pumpkins and scoop out the seeds and strings.
Rub the insides with 1 tablespoon olive oil and sprinkle lightly with salt and pepper.
Place pumpkins on a foil-lined baking sheet and roast for 20 to 25 minutes until just tender but still sturdy.
While pumpkins roast, heat the remaining 1 tablespoon olive oil in a large pot over medium heat.
Add the ground beef or turkey and cook until browned, breaking it up with a spoon. Drain excess fat if needed.
Stir in the onion, red bell pepper, and garlic and cook for about 5 minutes until softened.
Add the cubed pumpkin and cook for another 5 minutes. If using canned pumpkin purée, stir it in at this stage.
Add the black beans, kidney beans, diced tomatoes, tomato paste, and broth and stir well to combine.
Season with chili powder, cumin, smoked paprika, cinnamon, salt, pepper, and chipotle if using. Stir to blend.
Bring the mixture to a boil, then reduce heat to low.
Simmer uncovered for 30 to 40 minutes, stirring occasionally, until the pumpkin is tender and the chili is thickened.
Remove roasted pumpkins from the oven and let cool slightly so they are easier to handle.
Fill each roasted pumpkin about three-quarters full with hot pumpkin chili.
Rest the pumpkin lids slightly off to the side so steam escapes for a bubbling cauldron effect.
Serve immediately with toppings like shredded cheese, sour cream, green onions, or avocado. Guests can scrape the pumpkin flesh into each bite.