Chili Stuffed Acorn Squash

We are in the depths of squash season, and we wanted to feature an acorn squash as an entree since most of our uses for such ingredients are relegated to the realm of side dishes. The shape of this particular ingredient reminded us of a bowl, and its flavour has a natural sweetness…so we figured we’d try using it as a vessel to serve a nice spicy chili!

We opted to use our Coffee and Molasses Chili for this meal and top it off with cheddar cheese that my wife’s grandpa gave us. However, this shell of a recipe (ha! pun!) would most likely work with your favourite secret recipe chili to give it a fun twist rather than serving it over classics like rice, baked potatoes, or even spaghetti. Since we relied heavily on our oven to make this, we also made Roasted Asparagus as a side dish…but if you want to really keep a good fall theme, try Roasted Brussels Sprouts (why waste a hot oven when you can multi-task?).

Time: 60 Minutes


  • Acorn Squash
  • Your favourite chili (or try one of our Chili Recipes)
  • Cheese of your choice (we are using cheddar)


  • Begin to make your chili of choice
  • Preheat your oven to 375 degrees F, line a baking sheet with foil, and give the foil a quick oil spray.
  • Cut a thin slice off the very top and bottom of your squash so that it can lay flat on its ends. Then, cut the squash in half, and scoop out all the seeds and stringy unpleasantness.
  • Place your scooped out squash halves on your baking sheet, and give them a quick oil spray (or butter rub), and roast for about 40 minutes.
  • While your acorn squash is roasting, turn your attention back to making your chili
  • After about 40 minutes, the squash will have begun to soften. Pull it from the oven, and stuff it with your chili. Place back into the oven for another 10 minutes.
  • Add your cheese atop the chili, and melt it in the oven.
  • Plate, devour, and enjoy!

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