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Get a large pot on the stove and heat the olive oil in it over medium high heat. Brown the meat in it for about 5 minutes while you break it up with a spoon. While the meat cooks, spice it up with the chili powder, salt, cinnamon, nutmeg, smoked paprika, cumin and crushed red pepper.
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Add the onion, chipotles in adobo and fresh cilantro to the pot once the meat is cooked and let them get fragrant for a couple of minutes. Deglaze the pan with the apple cider vinegar, scraping up those yummy brown bits at the bottom of the pot.
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Add the pumpkin puree, crushed tomatoes and chicken stock into the pot and give the pumpkin chili a big stir. Bring it to a boil, then reduce it to a simmer and let it go low and slow for an hour.
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Scoop the chili into bowls, then top them off with a dollop of greek yogurt and a few fresh cilantro leaves. Enjoy the Fall inspired comfort!