Smoky Beef Chili with Winter Squash


Smoky Beef Chili with Winter Squash topped with sour cream, cheddar cheese, and pickled red onions and jalapeno peppers.

Most people’s prep list for severe weather conditions consists of candles, batteries, blankets, canned goods and flashlights. My mind was on blizzard food. Really tasty blizzard food. That’s what my house needed.

My husband offered to head to the food store late Monday afternoon to grab some groceries before the blizzard hit. Even though my lists are thoroughly nerdy (I list the items in the order he will happen upon them in the store to cut down on shopping time), the poor man ended up being stuck in a line an hour deep. We both agree it was worth the pain after tasting this chili. Smoky, spicy, full of depth with just a touch of sweetness from the squash and garlic, this recipe will be at the forefront of my mind the next time I happen to be stuck in snow two feet deep.

blizzard 2015

Our backyard on Tuesday morning. Not nearly as bad as we had expected.

Smoky Beef Chili with Winter Squash – adapted from smitten kitchen who first adapted it from Gourmet


  • 2 Tbsp olive oil
  • 1 large onion, chopped
  • 1 ½ cups butternut or other winter squash cut into a medium dice (½” cubes)
  • 25 cloves of garlic, 5 minced, 20 whole
  • 2 lbs beef, chopped
  • 4 Tbsp chili powder
  • 1 Tbsp cumin
  • 1 Tbsp oregano
  • ½ tsp smoked spanish paprika
  • 4 chipotle peppers in adobo sauce, chopped
  • 1 cup beef broth
  • 3 Tbsp apple cider vinegar
  • 14 oz crushed tomatoes
  • Toppings: sour cream, cheddar cheese, pickled , and pickled red onions

Heat olive oil in a large pot on medium. Add in the chopped onion and let cook on medium low for 5 minutes stirring occasionally. Add in the diced squash and cook for 8 more minutes stirring occasionally. Add in 5 cloves of whole garlic, 5 cloves of minced or microplaned, the 2 lbs of chopped meat, and 1 tsp salt. Raise heat to medium and cook until beef is no longer pink (about 8 min), stirring once in a while. Add the spices (chili powder, cumin, oregano, paprika), chipotle peppers, and remaining garlic cloves. Stir and cook for 2 more minutes. Stir in beef broth, apple cider vinegar, and crushed tomatoes. Lower heat to low, cover and let simmer for 35 minutes.

Garnish with sour cream, cheddar cheese, pickled jalapenos, and pickled red onions.

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