Coarsely chop tomatoes and apples. Mince garlic. Chop onion and mince chipotle, including seeds. Trim fat from pork. Cut meat into big chunks, about 2-in. (5-cm).
Coat a large wide saucepan with oil and set over medium heat. Add onion and garlic. Cook until softened, about 3 min. Add tomatoes, apples, chipotle and seasonings. Stir, then add pork. Increase heat to high and bring to a boil, stirring often. Then reduce to medium-low. Cover and simmer, stirring occasionally, until meat is tender, about 1 hour.
Meanwhile, to easily peel squash, make a large slit through skin with a knife, then microwave on high to soften skin a little, from 5 to 7 min. Remove squash from microwave. Peel, slice in half and discard seeds. Chop into small pieces, about 1-in. (2.5-cm). Chop pepper into similar-size pieces. Drain and rinse beans. Once pork has simmered 1 hour, stir in squash, pepper and beans. Cover and simmer, stirring occasionally, until pork is very tender and squash is soft, about 25 more min. Remove from heat. Stir in cilantro. Spoon into bowls and generously dollop with sour cream, if you wish.
Nutrition (per serving)
Apples, pork and cinnamon give chili a fall flavour makeover.