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Fall Chili with Sausage, Squash, & Apple

Updated: Aug 26, 2021

And a Happy Fall to you! I started writing this post by talking about the magic of fall and getting cozy, the joy of wearing warm, fuzzy socks and things like that, but when I asked Paul to read it and he rolled his eyes, I got it. Too much, no one is feeling that. This fall is weird and we're all dealing with A LOT. But I am still going to watch Harry Potter goddammit, carve a pumpkin and eat some candy corn.

One thing we can do for ourselves is make a big pot of fall chili (recipe link). It will last for a few days, longer if you freeze some, and it’ll provide that comfort we could all use more of.

This chili calls for squash and apple, sage, ginger, and cinnamon; flavors that define the start of the fall season. I developed this recipe five years ago for a chili cook-off and have been making it ever since. The prep work is a bit lengthy, but totally worth it. You'll end up with a lot of chili which can fuel you over the course of a few days, or freeze half of it for the winter. If you do the vegetable chopping a day in advance, you'll save time on the day of cooking. If done all at once, prep time takes about an hour and a half. I'm a slow chopper though, so you may not need as long. If you have a helper, that's ever better!


Serves 6-8


  • 2 pounds of pork sausage

  • 1 tablespoon fresh sage, finely chopped

  • 2 tablespoons crystalized ginger, finely chopped

  • 1 teaspoon cinnamon

  • ¼ cup bread crumbs

  • 6 strips of thick cut bacon

  • 2 tablespoons brown sugar

  • ½ teaspoon red pepper flakes

  • extra virgin olive oil (about ¼ cup)

  • 1 medium yellow onion, diced

  • 4 cloves of garlic, minced

  • 1 jalapeno, de-seeded & diced

  • 1 red bell pepper, de-seeded & chopped into ½” cubes

  • 2 Thai chili peppers (or 1 fish pepper), de-seeded & diced

  • 1 medium butternut squash, chopped into ½” cubes

  • 1 apple, honeycrisp or similar, chopped into ½” cubes

  • 1 - 16 oz can corn kernels, drained

  • 1 ½ tablespoons smoked paprika

  • ½ tablespoon cayenne

  • 1 tablespoon cumin

  • 1 - 28 ounce can of stewed San Marzano tomatoes

  • juice from half a lime

  • salt + pepper



1---Preheat oven to 400F. Place sausage in a large bowl and add the sage, crystallized ginger, cinnamon, breadcrumbs, salt & pepper, and massage into meat. Use a potato masher if the meat is too cold, or if you think of it in advance, take the meat out of the fridge half an hour ahead of time.

2---Lay the bacon on a medium sheet pan covered with crinkled foil or a wire rack. Sprinkle brown sugar and red pepper flakes over the bacon and bake for 15 minutes, or until crispy. Let cool before chopping into bite-sized pieces.


1---Put a large Dutch oven or stock pot over medium heat and add extra virgin olive oil, about ¼ cup. Once hot, add the peppers, onions, garlic and some salt + pepper and sauté for a few minutes, until they become aromatic. Add the sausage and begin separating the meat. This works best with a flat-ended wooden spoon, using a repetitive downward motion, push the spoon through the meat until hitting the pan and continue doing this until the meat browns, but does not cook through completely. Add the bacon, squash, apple, corn, paprika, cayenne, and cumin. Stir.

2---Open the can of San Marzano tomatoes, and using your hands, pull out the tomatoes one by one and gently squish out the juice from the centers into the can. Rough chop all tomatoes and add to the pot along with the juice from the can. Add about ½ cup of water and lime juice and stir to combine.

3---Cover and cook on simmer for 4 hours, stirring occasionally. Taste after a couple of hours and adjust with salt + pepper. The chili can also be done in a slow cooker, with the initial setting on high, then reduced to low for 6-8 hours once the final ingredients have been added. Serve with rice, egg noodles, or cornbread. I added 1 diced jalapeno, a handful of shredded cheddar, a few tablespoons of ricotta, and 1 cup of creamed corn (subbed for the vegetable oil) to a boxed mix and it was lovely. Enjoy!

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