Butternut Squash Chili is the perfect vegetarian one-pot meal. As delicious as it is pretty, it's full of smoky flavors, warming spices and hearty vegetables. It's a true bowl of plant-based comfort.
Roast and peel peppers: Turn on the broiler and adjust a rack a few inches below it. Cut each pepper in half lengthwise, and remove the seeds. Place them round side up on a foil-lined baking sheet and set it under the broiler until the skin is fairly evenly charred, about a minute. Remove them and then wrap them in the foil they're on, leaving some space for air inside. Let them steam this way for about 5 minutes. Use your hands or the dull side of a knife to remove the skin. Finely chop the peppers, and fill a ¼ cup measure with them. Set aside.
Prep and roast the squash: Adjust the oven rack back to the center of the oven and preheat to 475°F. Line a sheet pan with parchment paper.Cut about ½-inch off the bottom and top of the squash, stand it up, and use a Chef's knife to remove the skin, slicing downwards from the top, between the flesh and skin. Use a spoon to remove the seeds.Cut the squash into ¼ to ½-inch pieces and place them in a mixing bowl with 3 tablespoons of the olive oil, brown sugar, cinnamon and about ¾ teaspoon of salt. Mix so all of the pieces are evenly coated. Pour this onto the parchment-lined sheet pan and roast until golden brown, about 20 minutes. They should be flipped/mixed about halfway through the cooking time.
Cook the onion and garlic: While the squash is roasting, coat the bottom of a large stock pot or Dutch oven with the remaining olive oil (and more if necessary). Add the onion and garlic and over medium heat, cook until the onion begins to brown, about 7 minutes.
Add peppers and spices: Add the ¼ cup of finely chopped jalapeños, along with the chipotles, cumin, and chili powder. Cook until it becomes very aromatic, about 1 minute.
Deglaze the pan: Then turn the heat to low and add the wine. Then turn the heat up to medium-high and cook until the wine is reduced by about half, about 4 minutes.
Add remaining ingredients and squash. Add the tomatoes, beans, and roasted squash. Turn the heat to low, cover, and simmer for about 15 minutes to blend all of the flavors.
Season: Add the oregano and season to taste with salt and pepper. (I usually add about 1 teaspoon of Kosher salt. If you use table salt, use half as much.)
If desired, serve with toppings (avocado, cheddar cheese, red onion, sour cream)
Notes
Nutritional information is automatically calculated, so it should only be used as an estimate.