Cut the sugar pie pumpkin in half, and scoop out the guts and seeds. Very lightly drizzle the pumpkin “bowl” with olive oil plus a sprinkle of salt and pepper. Then place the pumpkin halves on a baking sheet, flesh side down. Poke the back skin side of the pumpkin with a sharp knife in a few places.
Roast the pumpkin on 400F for approximately 40 to 45 minutes, until soft. If you’re using canned pumpkin, skip right to Step 4.
Once the pumpkin has finished roasting and cooled slightly, remove the skin and discard.
Combine diced onion, mushrooms, bell pepper, salt and black pepper in a large pot on the stovetop - along with a good splash of olive oil. Over medium-high heat, cook until everything softens and the onions are translucent - about 5 minutes. Stir occasionally.
Next, add diced garlic, oregano, soy sauce, and other seasonings listed above to the pot. Mix well to coat. Allow to cook for another few minutes.
Pour in the called-for veggie broth, tomatoes (with juices), and beans (strained, without the can liquid) into the pot. If your pumpkin is thoroughly cooked and very soft, you can toss it into the pot in large chunks. If it still seems a little firm, mash it up in a bowl first to break it apart. Mix well.
Once everything is combined, bring the pot to a boil. Thereafter, reduce the heat to simmer for a final 15 to 20 minutes, until it has thickened and reduced to your liking.
Serve and enjoy! Delicious and popular chili toppings include crunched tortilla chips, avocado, grated cheese, fresh cilantro, pumpkin seeds, sour cream, or even microgreens. It is also amazing with homemade sourdough bread.
Enjoy within one week if stored in the refrigerator, or freeze some to enjoy for months to come! Allow the chili to cool slightly before packaging. Defrost frozen pumpkin chili in the refrigerator a day or two before you want it, and simply reheat on the stovetop in a pot.