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Heat the beans on top of the stove in a large soup pot or Dutch oven.
Heat the oil over medium heat in a heavy nonstick skillet and add the onion, carrot and pepper. Cook, stirring often, until the vegetables are tender and beginning to color, about 8 minutes. Stir in the garlic, stir together until fragrant, 30 seconds to a minute, and add the ground chili and cumin. Cook, stirring, for 2 to 3 minutes, until the mixture begins to stick to the pan. Add the tomatoes and oregano, and salt to taste. Bring to a simmer and cook, stirring often, until the tomatoes have cooked down and the mixture is beginning to stick to the pan, about 10 minutes. Stir in the tomato paste dissolved in water and bring back to a simmer. Season with salt to taste and simmer, stirring often, for 10 minutes, until the mixture is thick and fragrant.
Stir the tomato mixture into the beans. Add the winter squash and bring to a simmer. Simmer, stirring often, for 30 to 45 minutes. It is important to stir often so that the chili doesn’t settle and stick to the bottom of the pot. It should be thick; if you desire you can thin out with water. Taste and adjust salt.
Shortly before serving stir in the cilantro and simmer for 5 minutes. Spoon into bowls. If you wish, top with grated cheddar, Monterey jack, or crumbled queso fresco.