Butternut Squash and Sausage Chili

Ethan is in seventh grade. He is in a different building, eating lunch at a different time, navigating hallways I have not seen with people I do not know, and he came home Tuesday with the slightly dazed quality of someone who has survived a larger thing than they expected. I made grilled cheese sandwiches for after-school snack because grilled cheese sandwiches are the most reliable comfort food in this family's lexicon, and I watched him eat two of them at the kitchen counter without saying much of anything, and I thought: he is going to be fine. He just needs a week to let his body catch up to the new situation. His body does this. So does mine.

Lily started second grade and came home Monday full of facts about her teacher, whose name I now know and whose classroom organization system Lily described in enough detail that I have a clear picture of both the room and the teacher's personality. Lily notices things. She has always noticed things. It is one of her gifts and one of the things about her that will someday be a superpower and right now is mostly charming.

Noah's preschool orientation is Friday. I have been told that orientation is thirty minutes of the parents meeting the teacher while the children play. I have been preparing Noah for this event the way you prepare someone for a theater audition: emphasizing strengths, recommending against his opening bit, which involves asking adults if they have ever seen a dinosaur eat a cracker. He has already memorized his teacher's name. He practiced introducing himself four times on Thursday. He is four and entirely prepared.

Sunday prep this week was a return to the oven: the heat has broken enough that I can run it without the kitchen becoming uninhabitable. First oven session since June. I made a double batch of white chicken chili, four bags of meatball marinara, and a full sheet pan of enchiladas baked and then portioned and frozen in squares. It felt like coming home to a part of my kitchen I had been missing. The smell of something baking after months of cold prep is a specific pleasure, the kind that belongs to the shift between seasons.

That first oven session reminded me how much I’d missed this kind of cooking—the slow, layered kind where the house fills up with something warm while the kids settle into their new routines. The white chicken chili was the headliner that Sunday, but this butternut squash and sausage chili has become the one I come back to when the season truly turns. It’s the kind of recipe that makes a double batch without complaint, freezes in perfect portions, and tastes like the specific comfort of a kitchen that’s finally cool enough to use again.

Prep Time: 20 minutes | Cook Time: 45 minutes | Total Time: 1 hour 5 minutes | Servings: 8

Ingredients

1 pound Italian sausage (mild or hot), casings removed
1 tablespoon olive oil
1 large yellow onion, diced
4 cloves garlic, minced
1 medium butternut squash (about 3 pounds), peeled, seeded, and cut into 1/2-inch cubes
2 cans (15 ounces each) kidney beans, drained and rinsed
1 can (28 ounces) crushed tomatoes
1 can (15 ounces) diced tomatoes with juices
2 cups chicken broth
2 tablespoons chili powder
1 tablespoon cumin
1 teaspoon smoked paprika
1/2 teaspoon cinnamon
1/2 teaspoon salt, plus more to taste
1/4 teaspoon black pepper
Pinch of cayenne pepper (optional)

Instructions

Brown the sausage. Heat olive oil in a large Dutch oven or heavy-bottomed pot over medium-high heat. Add sausage, breaking it into crumbles with a wooden spoon, and cook until browned, about 6–8 minutes. Transfer to a plate.
Cook the aromatics. In the same pot, add the diced onion and cook until softened, about 4 minutes. Add garlic and cook 1 minute more until fragrant.
Add spices and squash. Stir in the chili powder, cumin, smoked paprika, cinnamon, salt, pepper, and cayenne. Cook for 30 seconds to bloom the spices. Add the cubed butternut squash and stir to coat.
Build the chili. Return the sausage to the pot. Add the crushed tomatoes, diced tomatoes, kidney beans, and chicken broth. Stir to combine and bring to a boil.
Simmer until tender. Reduce heat to medium-low, cover with the lid slightly ajar, and simmer for 30–35 minutes, stirring occasionally, until the squash is fork-tender and the chili has thickened.
Adjust and serve. Taste and adjust salt and spices. Serve hot, topped with sour cream, shredded cheese, or diced avocado if desired. Chili freezes well in portioned containers for up to 3 months.

Nutrition (per serving)

Butternut Squash and Sausage Chili — The First Oven Session Since June