Roasted Squash, Kale and Tomato

I was getting pretty sick of the same old ways to cook winter squash and came up with this combination. Not a soup; rather, more of a hearty side dish or a filling yet healthy lunch.


  • 1 kabocha squash or other winter squash
  • Extra virgin olive oil (EVOO)
  • 1 onion
  • 3 cloves garlic
  • 1 pint grape tomatoes or cherry tomatoes
  • 1 bunch dinosaur kale or other leafy green that isn’t bitter
  • 1 cup chicken stock
  • 1/2 teaspoon smoky paprika
  • 1/4 teaspoon dried red chili seeds
  • Salt and pepper, to taste


Pre-heat the oven to 350°F. 

Split open the squash and scoop out the seeds. Cut the squash into big pieces and slather it with EVOO and sprinkle with salt. Roast until soft, about 45 minutes.

When cool enough to handle, cut the squash away from the peel and cut into chunks.

Cover the bottom of a heavy-bottomed saucepan with EVOO. Bring the heat to medium high. Chop the onion and add to the pot, stirring for a few minutes. Chop the garlic cloves and add to pot. Cut the tomatoes in half and add to pot. Stir frequently, so that the garlic doesn’t burn, and cook until the tomatoes start to burst. Add the squash, stir completely and add the stock.

Meanwhile, clean the kale; chop into 1-inch pieces and add to the pot. Add seasonings and cover. Reduce the heat to a simmer and let it go until the tomatoes are completely burst and mushy and the flavors are all blended nicely. If too liquidy, you can remove the cover and let it cook for a few minutes uncovered so that the liquid evaporates.

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