Beef and butternut squash chili is nothing new around here. I posted a recipe for the same combination last year (recipe HERE) but it’s such a good one it’s worth repeating, with variations.
My original recipe includes peppers and black beans and is a really delicious one pot meal. The version I’m sharing with you today is simpler at its core and a bit less traditional with a collection of rather uncommon, but totally delicious toppings.
With football playoffs upon us and the Super Bowl approaching, this chili and toppings would make an amazing chili bar, and I love that guests would have a collection of toppings that’s out of the ordinary. It’s the perfect balance of crunchy, creamy, and tangy tangled on top of a succulent pulled beef chili.
It all starts with my easiest beef roast ever recipe (HERE), which I make a few days before I plan to make this chili. Once that’s done, this chili is so easy. You prep the toppings while the chili is simmering and it’s all on the table in about 30 minutes.
Beef and Butternut Chili with Uncommon Fixings
1 red onion, cut in half through the root and then in 1/4″ slices
apple cider vinegar
1 tbsp. sugar
1 tbsp. olive oil
1 c. yellow onion, chopped
4 cloves garlic, minced
2 tsp. chili powder
2 tsp. cumin
1 tsp. oregano
12 oz. bottle of beer (I used an IPA)
2 4-oz. cans chopped mild chiles (or hot if you want more heat)
4 c. red wine broth left from beef roast, or canned beef broth if you don’t have the reserved or need to supplement
2 c. butternut squash, peeled and chopped into 1/2″ chunks
4 c. reserved shredded chuck roast
toasted and salted pumpkin seeds
diced or sliced avocado
Place the red onion in a microwave safe bowl and pour in enough apple cider vinegar to come about halfway up the onions. Sprinkle with sugar and add water to cover. Microwave 2 minutes then set aside to soak while you prepare the rest of the chili.
Heat olive oil in a large pot or dutch oven over medium-high heat. Add yellow onion and cook until translucent, about 5 minutes. Add garlic and cook 1 minute longer.
Add chili powder, cumin, and oregano and stir into the onions and garlic.
Pour the beer into the pot and use a wooden spoon to scrape up any browned bits.
Add the canned chiles and broth and raise heat to high.
Stir in the butternut squash and beef and bring to a boil, then lower heat and simmer until squash is tender, 10-15 minutes.
Drain the red onions and place in a small bowl.
Ladle the chili into bowls and serve topped with yogurt, pickled red onions, avocado, pumpkin seeds, and cilantro.