
This hearty Pumpkin Chili with Cheddar Web Top has become my favorite way to celebrate autumn's arrival while making dinner fun for the whole family. Sweet pumpkin and savory meat meld with cozy beans and spices, and the playful cheddar spiderweb on top always gets smiles at our table especially for Halloween.
I whipped this up on a rainy fall weekend as a way to use up leftover pumpkin and my kids fell in love with the cheesy web there is never any chili left when I make it this way
Ingredients
- Ground beef or turkey: brings rich flavor and extra protein choose lean meat for less grease
- Olive oil: helps sauté veggies for depth and healthy fats use a fruity variety for best taste
- Onion: sweetens the chili and gives body pick firm onions with tight skins
- Red bell pepper: adds color and gentle sweetness select a glossy pepper for maximum freshness
- Garlic: infuses warmth and aroma use fresh cloves over pre-minced
- Pumpkin: either fresh diced or good-quality canned purée delivers autumn character and sweetness
- Black beans and kidney beans: provide heartiness pick canned beans that are simply salted without additives
- Diced tomatoes: add tang and sauciness opt for fire-roasted for deeper flavor
- Low-sodium beef or vegetable broth: balances salt and lets spices shine check labels for gluten-free purity
- Tomato paste: boosts umami and helps thicken always go for double-concentrated if you can
- Chili powder: brings heat and smoky allure taste it before adding for potency
- Cumin: adds earthy depth freshly ground gives more punch
- Smoked paprika: gives a subtle smoky note hunt for Spanish style if possible
- Cinnamon: rounds out the flavors with gentle warmth use true Ceylon if you have it
- Salt and black pepper: for seasoning start modest and adjust
- Cayenne pepper: optional for those who crave a little extra kick
- Sharp cheddar cheese: makes the fun and flavor at the end shred yourself for best melting
Instructions
- Brown the Meat:
- Heat olive oil in a large pot over medium heat. Add the ground beef breaking it up with a wooden spoon. Let it cook fully until no pink remains about seven minutes. Drain any excess fat to keep the chili from getting greasy.
- Build the Vegetable Base:
- Add diced onion red bell pepper and minced garlic to the pot. Sauté on medium until the onion softens and turns translucent about five minutes. This step locks in flavor and makes the chili aromatic.
- Incorporate Pumpkin:
- Tip in your diced pumpkin and stir frequently for three or four minutes. This helps the pumpkin begin to soften and mingle flavors before the liquids go in.
- Toast the Spices:
- Add tomato paste chili powder cumin smoked paprika cinnamon salt black pepper and cayenne if desired. Stir everything well so the spices coat all the vegetables and meat. Keep stirring for two minutes to bring out the spices' fragrance and deepen the flavor.
- Simmer the Chili:
- Pour in diced tomatoes black beans kidney beans and broth. Scrape the bottom of the pot to lift any browned bits. Bring to a boil then turn down the heat and let simmer uncovered for thirty to thirty-five minutes. Stir occasionally and check that the pumpkin becomes fork-tender and the chili thickens.
- Adjust to Taste:
- Spoon up a little chili and taste for seasoning. Add more salt pepper or heat as preferred.
- Create the Cheddar Web:
- Ladle hot chili into ovenproof bowls. Arrange shredded cheddar in a web pattern on top. Use a piping bag for concentric circles and then gently drag lines outward with a knife for a spiderweb look.
- Broil for Bubbly Cheese:
- Place bowls under a preheated broiler for two or three minutes until cheese just melts and bubbles. Watch closely so the cheese turns golden but does not burn. Serve immediately so everyone can enjoy the gooey cheddar web.

The pumpkin here is the real star I love how it adds a gentle sweetness and fits so well with chili spices. My kids still talk about the night they tried to copy my cheddar web decoration—we laughed so hard at our different cheese "spiders".
Storage Tips
Keep leftover chili tightly covered in the fridge for up to four days. Reheat slowly so beans do not burst. The cheese web is best enjoyed fresh but you can melt more cheddar on reheating. Freeze cooled chili in portions for up to two months making it a smart choice for busy weeks.
Ingredient Substitutions
Try ground turkey or chicken instead of beef for a lighter taste. Use canned pumpkin purée for speed but fresh pumpkin cubes give extra texture. Substitute pinto beans for kidney if preferred or toss in lentils for a boost. Veggie broth works well for a plant-based version.
Serving Suggestions
This chili loves a side of crusty bread warm cornbread or crunchy tortilla chips for dipping. A light green salad balances meal richness and sweet apple cider adds a festive touch. It is a wonderful centerpiece for fall get-togethers or spooky Halloween suppers.
Cultural and Historical Notes
Pumpkin chili is a modern twist that combines Native American traditions of cooking pumpkins and beans with classic American chili. The cheddar web started as a playful Halloween garnish but now it is a favorite in our house for autumn dinners. Chili itself remains a beloved comfort dish across the US.

Enjoy this festive chili for chilly evenings and fall celebrations. The cheddar web adds plenty of smiles to every bowl!
Common Questions About Recipes
- → Can I substitute fresh pumpkin with canned pumpkin?
Yes, canned pumpkin purée works well. Add 1 cup during simmering for a smooth texture.
- → What beans work best for this chili?
Black beans and kidney beans provide hearty texture. Feel free to add extra varieties or lentils.
- → How can I make this meal vegetarian?
Simply leave out the meat and increase beans or add lentils for protein and flavor.
- → How do I create the cheddar web topping?
Arrange shredded cheddar in a web pattern using a piping bag or layer circles and lines before broiling.
- → What wine pairs best with this dish?
Try a fruity Zinfandel or Malbec to complement the chili’s spicy notes and cheddar topping.
- → Is this meal suitable for gluten-free diets?
Yes, as long as you use certified gluten-free broth and check your cheese labels.