Butternut Squash Chili Delight

This butternut squash chili brings together smoky spices, sweet roasted squash, and hearty beans into a comforting vegetarian stew that feels like a warm hug on a chilly day. It’s designed to be a one main cooking vessel meal full of flavor and texture, making it perfect for weeknight dinners or meal prep when you want something satisfying and packed with nutrients.

This recipe instantly became a favorite when I made it on a cold, snowy evening. The warmth and complexity of the spices filled the house, and my family couldn’t get enough. Now it pops up regularly whenever I want a meatless meal that feels just as hearty.

Ingredients

• Jalapeño peppers: roasted and peeled to bring a smoky heat that’s not overpowering. Look for firm peppers with bright skin for roasting.
• Butternut squash: peeled and diced to provide sweetness and a creamy texture that holds up well when roasted. Choose a squash that feels heavy with a matte exterior to ensure ripeness.
• Olive oil: used in parts helps roast the squash and sauté the aromatics, adding richness and depth. Use good quality extra virgin olive oil if possible.
• Brown sugar: balances the savory and spicy notes with a touch of caramel sweetness.
• Ground cinnamon: adds warmth and complexity; fresh ground offers the best aroma.
• Onion and garlic: finely chopped onion and minced garlic build the aromatic base of the chili. Fresh, firm onions and garlic bulbs guarantee the best flavor.
• Chipotles in adobo sauce: give a smoky, slightly spicy punch; check the label for quality and avoid those with preservatives.
• Ground cumin and chili powder: layer in classic chili spice flavors for depth. Look for spice blends without fillers.
• Dry red wine: to deglaze the pan and add a subtle fruity note (Cabernet or Merlot works well). If you prefer not to use wine, robust vegetable broth can be a substitute.
• Canned diced tomatoes and beans: two types of beans, kidney and Cannellini, add texture, protein, and body. Choose low sodium beans to control the salt level.
• Fresh oregano: enhances the herbaceous freshness at the end; always wash and dry herbs properly before chopping.
• Salt and pepper: to balance and bring out flavors.
• Optional toppings: avocado and cheddar cheese bring richness and creaminess for serving.

Instructions

Roast and peel peppers:

Turn on the broiler and position a rack just a few inches below it. Halve the jalapeños lengthwise and remove the seeds carefully to reduce heat. Place the peppers skin side up on a foil lined baking sheet. Broil until the skins are charred and blistered, about a minute. Remove the peppers and wrap them loosely in the foil to let them steam for about five minutes. Steam to loosen the skins, then peel and finely chop the peppers and measure out about a quarter cup to use later. Set aside.

Prep and roast the squash:

Preheat the oven to 475 degrees Fahrenheit and move the oven rack to the center position. Line a baking sheet with parchment paper. Trim the very top and bottom ends from the squash and remove the outer skin in strips. Cut the squash in half and scoop out the seeds, then cut the flesh into roughly halfinch dice to ensure even roasting. Toss the diced squash with three tablespoons of olive oil, the brown sugar, cinnamon, and about three quarters of a teaspoon of salt. Spread in a single layer on the prepared sheet pan and roast for about twenty minutes, turning the pieces halfway through so they brown evenly. Aim for golden tender but not mushy pieces.

Cook the onion and garlic:

While the squash roasts, coat the base of a large Dutch oven or heavybottomed pot with the remaining olive oil. Add the chopped onions and minced garlic and cook over medium heat for about seven minutes, stirring occasionally, until the onions soften and begin to turn golden brown.

Add peppers and spices:

Stir in the quarter cup of roasted jalapeños along with the chopped chipotles in adobo, ground cumin, and chili powder. Cook just a minute until the mixture becomes very fragrant.

Deglaze the pan:

Lower the heat and pour in the dry red wine to deglaze. Then bring the heat back up to mediumhigh and cook until the wine reduces by about half to concentrate the flavors and dissolve browned bits.

Add remaining ingredients and squash:

Add the canned diced tomatoes with their juices, both drained types of beans, and the roasted squash to the pot. Stir gently to combine, lower to a simmer, cover, and cook for about fifteen minutes to let flavors meld and heat the beans through.

Season:

Chop fresh oregano and add it along with salt and black pepper to taste. Adjust seasoning as needed and offer optional toppings like sliced avocado, shredded cheddar cheese, finely diced red onion, or a dollop of sour cream for serving.

One of my fondest memories with this recipe involves making a big batch for a family gathering where everyone reached for seconds and thirds, even those who usually prefer meat were won over by the hearty, smoky, and sweet layers of flavor.

Storage tips

Store any leftovers in airtight containers in the refrigerator for up to four days. This chili tastes even better the next day as the flavors have more time to meld. You can also freeze portions for up to three months and thaw overnight in the fridge before reheating gently on the stove over low heat.

Ingredient substitutions

If you cannot find chipotles in adobo sauce, smoked paprika can offer a milder smoky punch though it lacks the heat level. Canned beans can be swapped for cooked dry beans if you prefer fresh. Red wine can be replaced with vegetable broth or apple cider for a different flavor profile.

Serving suggestions

Serve your chili over fluffy rice or with warm cornbread on the side. Topping it with sliced avocado, a sprinkle of sharp cheddar, or a spoonful of sour cream brings a delicious contrast to the bold chili spices.

This hearty, smoky chili is perfect for cozy dinners and makes great leftovers. Top and serve as you like.

Common Questions About Recipes

→ How do I roast the butternut squash effectively?

Peel and dice the squash into ½-inch pieces, toss with olive oil, brown sugar, cinnamon, and salt, then roast at 475°F until golden, flipping halfway.

→ What does roasting the jalapeño peppers add to the dish?

Roasting softens the peppers, adds smoky depth, and mellows the heat, enhancing the overall flavor profile.

→ Can I use other beans instead of kidney and Cannellini beans?

Yes, other sturdy beans like black beans or pinto beans work well and complement the spices and squash.

→ What is the purpose of deglazing with red wine?

Deglazing lifts browned bits from the pan, adding complexity and rich flavor while balancing the spicy elements.

→ What are some recommended toppings to serve with this dish?

Avocado, sharp cheddar, red onion, and a dollop of sour cream provide contrast in texture and enhance creaminess.