Chili Stuffed Acorn Squash

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There is just something so enjoyable about one dish meals to me, especially one dish meals that you can actually eat the dish that it is served in!  We eat a lot of chili in this house.  I know it is more of a warming winter dish, but what I love most about chili is that you can make it all times of the year and adapt the ingredients to whichever season it is.

I’ve seen a lot of chili recipes that use butternut squash or other winter vegetables, but I decided to mix it up a little bit and make my traditional chili recipe and serve it inside of this roasted acorn squash.  Don’t you just love it when soups or stews are served inside of edible bowls?!  This way you get a little bit of acorn squash in every single bite!

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I feel like I haven’t been eating nearly enough winter squash this season, but my excuse is that it has been sunny and 80 here the last few weeks and I haven’t exactly been in the mood for hot foods.  It is kinda crazy to me that other parts of the country are getting tons of snow and ice and I’m breaking a sweat while checking the mail!  It makes it hard to really feel like cooking seasonal recipes for the blog because all I can think about is grilling and eating salads on the patio.  But, as I said before, chili is one of those recipes that I like to eat all year round just because it is so darn tasty.  So, I hope that you will enjoy this recipe whether you are buried in 20 feet of snow or packing those winter coats away to make room for the shorts and t-shirts :)

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Chili Stuffed Acorn Squash

  • Prep Time: 20 mins
  • Cook Time: 40 mins
  • Total Time: 1 hour
  • Yield: 4
  • Category: Entree, Gluten Free, Vegan


  • 2 whole acorn squash
  • 1 teaspoon olive oil, plus more for roasting acorn squash
  • 2/3 cup diced onion
  • 2 clove garlic, minced
  • 1/2 cup diced red pepper
  • 1/2 cup diced green pepper
  • 1 cup diced tomato
  • 1 1/4 teaspoon salt
  • 1/4 teaspoon black pepper
  • 3 cups cooked beans, I used 1 can pinto and 1 can kidney
  • 2 tablespoons tomato taste
  • 2 teaspoons chili powder
  • 2 teaspoons cumin
  • 1 teaspoon paprika
  • 1/4 teaspoon smoked paprika
  • 1/2 teaspoon dried oregano
  • 1/2 teaspoon brown sugar, or coconut sugar
  • 1 tablespoon water, or more depending on how thick you want your chili
  • Cilantro, for garnish if desired


  1. Pre-heat the oven to 375 degrees Fahrenheit. Cut the acorn squash in half, lengthwise, and scoop out the seeds. Drizzle the insides with a small amount of olive oil and season with salt and pepper. Place the squash, cut side down, in an oven safe dish and fill with 1/4 inch water. Bake squash for 30-40 minutes, until tender.
  2. While squash is baking, make the chili. Heat a large pot over medium heat and drizzle with olive oil. Add the onion, garlic, peppers, tomato, salt and pepper and stir for 3-5 minutes until tender. Add the remaining chili ingredients. Stir until everything is combined and simmer until squash is finished baking.
  3. Once squash is done, scoop about 1 cup of chili into each squash bowl. Top with your favorite chili toppings.


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    • She Likes Food says

      Thank you, Kelly! Oh no! It sounds like it is really cold where you live! As jealous as I am of your snow, I’m not sure I could handle it being so cold after living in AZ for the past two years :) Stay warm!

    • She Likes Food says

      I’m gonna go check yours out right now, Katie! I love chili so much and am always looking for different chili recipes to try out :) I hope you are staying warm!

  1. says

    I love the idea to stuff acorn squash with chili — it sounds like the perfect combination! I think it’s fun to eat a meal like this too…out of an edible bowl! It’s been really warm here too, but I’m strange in that I could eat chili and soup all year no matter what the temp is. This needs to be dinner! :)

    • She Likes Food says

      It is so good together, Marcie! I wonder why it is so warm so early?! I hope it isn’t a sign of what is to come this summer! I can eat chili all year round too :)

  2. says

    This is such a smart idea! Edible bowls are the best. But this is much healthier than the usual bread bowl. Now that I think about it, I haven’t made acorn squash once all year! Going to have to change that asap : )

    • She Likes Food says

      I feel slightly bad that I was just complaining that it was too cold when it was 70 degrees, but your body really does get use to the hot temps, haha!

  3. says

    I only cooked squash like 3 times this winter, so I need to make some pretty soon! Turfing it with chili sounds delicious! Awesome idea, pinned!

  4. says

    I absolutely love the idea of a one dish meal where you can eat the ENTIRE thing! That means there are less dishes to do, right?! :) This squash looks gorgeous! I definitely haven’t had enough of it this year, so you are inspiring me to get on that. And chili seems like the perfect addition, especially for the winter!

    • She Likes Food says

      Definitely less dishes involved! Or at least I like to pretend there are :) I know! I feel like I’ve forgotten a little bit about squash this winter and it is already getting warm around here. I guess there is always next winter :)

    • She Likes Food says

      Thank you so much, Sarah!! I knew you would love this being a fellow chili lover! It really doesn’t get much better, does it?! :)

  5. says

    What gorgeous photos … and stuffed squash, of course (that goes without saying!)
    It really is hard to imagine you sweating it out over there. I must say I’m jealous, though – it’s so gloomy here!

    • She Likes Food says

      Thanks so much, Helen! I think I might be jealous of your weather too, haha! As much as I’m enjoying the warm weather I can’t help but be sad that our winter is pretty much over and soon it will be 100 degrees and these stuffed squash will be the last thing on my mind :)

  6. says

    I took a bit of a winter squash break, but I think I’m ready to get back into it! These chili stuffed bowls sound so tasty! The perfect blend of sweet squash and spicy chili.

    • She Likes Food says

      I need to get back into it before winter is over and then I have to wait until next year! Thank you! You are so right, the sweet squash and spicy chili go so well together!

  7. says

    Yup, year round chili eater here too! It’s soooo good and I love how you’ve used an acorn squash as a bowl. I’ve got one left from my winter CSA…. it NEEDS to be used. But alas, Rob is not agreeable to squash which makes it harder for me to be creative with them because I know he’ll resist. But I am determined to get around this block and just make it! They’re so delicious, especially when chili is involved (and look at the paprika in there, yay!!). Thanks Izzy!

    • She Likes Food says

      Haha, I definitely served Eric’s chili in a regular old bowl, no run acorn squash bowl for him!! I probably could have gotten him to eat it if I can chopped up the squash and put it in the chili, but it just didn’t have the fun look I was going for! Besides, only boring food would be made if I catered to him all the time :) I think I’ve been putting paprika in everything lately :) I might have a big of a problem…

    • She Likes Food says

      You should totally try it, Denise! So good! and so cute! You should move down here! Although I think I’m getting way too soft because it was 70 degrees here today and I was all bundled up and shivering :)


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