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In a large Dutch oven, heat 1 tablespoon oil over medium-high heat. Add sausage; cook for 5 to 6 minutes until browned, stirring occasionally. Remove sausage with a slotted spoon.
In the same pot, cook onions and garlic for 2 to 3 minutes, stirring occasionally, until nearly tender. Add squash; cook for 5 minutes. Stir in chili powder, salt and cayenne; cook for 1 minute. Return the sausage to the pot. Add broth; bring to a boil, then reduce heat. Simmer, covered, for 8 minutes.
Meanwhile, in a large skillet, heat the remaining 1 tablespoon oil over medium-high heat. Add apple slices; cook for 4 to 5 minutes, stirring occasionally, until light brown. Transfer the apples to the chili. Stir in beans. Simmer for 3 to 4 minutes until apples are tender. Top servings of chili with sage and apple rings.