Turkey Chili with Roasted Butternut Squash
Roast butternut squash cubes with olive oil, chili powder, cinnamon, salt and pepper at 450Β° for about 20 minutes. Cook the onion, peppers and garlic in olive oil until soft, then add the ground turkey and brown it, breaking up the clumps. Season with salt, pepper and chili powder, stir in Worcestershire and hot pepper sauce, then add the crushed tomatoes, chili sauce, tomato paste and beans. Simmer on low for 20 minutes, adjust the seasonings and top each bowl with the squash.
When the weather turns and the house fills with people, few things are as welcome as a big pot of chili. This one leans lighter with turkey but loses nothing in comfort, and the addition of cinnamon-roasted butternut squash gives it a gentle sweetness and autumn warmth that sets it apart. It simmers happily on the stove, growing richer by the minute, ready to ladle into bowls for anyone who wanders in cold and hungry.
Cinnamon-Roasting the Squash
Roast the butternut squash with a touch of cinnamon until the edges caramelize and the sweetness deepens — roasting first keeps the pieces intact and concentrates their flavor. Spooned over each bowl at the table, they bring little pockets of warm sweetness that play beautifully against the savory chili.
Building the Chili
Brown the turkey with the aromatics, then add your spices, beans, and liquids and let the whole pot simmer until it is thick and deeply flavored. A 20-minute simmer is what melds everything together, so give it time and taste as you go — the roasted squash goes on at the very end, spooned over each serving.

Turkey Chili with Roasted Butternut Squash
Ingredients
- 1 medium butternut squash, peeled, seeded, and cut into 1-inch cubes, about 3 to 4 cups
- 2 tablespoons olive oil
- 1 tablespoon ground chili powder
- 1 teaspoon ground cinnamon
- 2 teaspoons kosher salt
- 2 teaspoons coarse black pepper
- 3 tablespoons olive oil
- 2 large onions, peeled and diced into Β½-inch pieces, about 3 cups
- 1 green bell pepper, seeded and cut into Β½-inch pieces, about 1 cup
- 2 large jalapeΓ±o peppers, seeded, deveined, and finely diced, about Β½ cup
- 6 to 8 garlic cloves, peeled and chopped, about ΒΌ cup
- 3 pounds ground turkey (a mixture of white and dark meat)
- 3 tablespoons (or more) ground chili powder
- 2 tablespoons Worcestershire sauce
- 4 to 6 drops (or more) hot pepper sauce
- 2 (28-ounce) cans crushed tomatoes
- 1 (12-ounce) jar chili sauce
- 1 (6-ounce) can tomato paste
- 1 (15-ounce) can black beans, drained and rinsed
- 1 (15-ounce) can red kidney beans, drained and rinsed
Method
- Preheat your oven to 450Β°.
- Lay the butternut squash pieces on a baking sheet.
- Drizzle with 2 tablespoons olive oil.
- Sprinkle on 1 tablespoon ground chili powder and 1 teaspoon ground cinnamon.
- Season with some of the salt and pepper.
- Use your (very clean) hands to gently toss the squash in the seasonings.
- Roast until the squash is soft and beginning to turn golden, about 20 minutes.
- Remove from the oven.
- Heat 2 more tablespoons olive oil in a large pot over medium-high heat.
- Add the onion, peppers, and garlic and cook until the veggies are soft and beginning to brown, about 8 to 10 minutes. Stir occasionally while cooking.
- Add another tablespoon olive oil to the pot.
- Add the ground turkey and cook, breaking up the clumps until the turkey is beginning to brown, about another 8 to 10 minutes.
- Generously season the turkey with salt, pepper, and 3 tablespoons chili powder. You can add more later if needed!
- Stir in Worcestershire and hot pepper sauce.
- Pour in crushed tomatoes and chili sauce.
- Stir in tomato paste.
- Add the beans.
- Reduce the temperature to low and simmer for 20 minutes.
- Stir, taste, and adjust the seasonings.
- Ladle the chili into bowls.
- Spoon roasted butternut squash on the top and dig in!
The Heart of the Table
A pot of chili is hospitality at its most generous — it stretches to feed whoever shows up and only gets better as it sits. Setting out a big pot with bowls and toppings tells a crowd to make themselves at home, help themselves, and stay warm as long as they like. It is comfort meant to be shared by the ladleful.
The Art of the Host
Simmer the chili on low, and keep the roasted squash in its own bowl so the pieces keep their shape — spoon it over as you ladle. Set out a spread of toppings — diced avocado, sour cream, red onion, pickled jalapeño and corn chips — so everyone can dress their own bowl, and keep the pot warm for the inevitable seconds.
Neighborly Grace
- The Preparation: Chili is the ultimate make-ahead; it deepens in flavor overnight and rewarms beautifully. Roast the squash ahead as well, and simply warm it through while the pot reheats — this is a dish that rewards being made a day early.
- The Pour: A robust Zinfandel or a dark amber ale stands up to the hearty, spiced chili; for a non-alcoholic option, a spiced apple cider served warm carries the same cozy, autumnal warmth.
- The Vibe: Serve it buffet-style from the pot with a table of toppings and plenty of cornbread, letting everyone build their own bowl. This is casual, come-as-you-are comfort — the kind of meal that suits a chilly afternoon, a full house, and no particular schedule.