Chili Maple Roasted Winter Squash is winter squash roasted to perfection with chili powder and maple syrup, tossed in an orange maple vinaigrette.  It’s sweet and spicy, and is a side dish that no one will forget!

Chili Maple Roasted Winter Squash |

Happy first day of fall!  This is my favorite season hands-down, and I get downright giddy when I start seeing all the gorgeous varieties of winter squash.  Clearly it doesn’t take much to get me excited, but can you blame me?  The colors are so pretty I can hardly stand it.

Just so you know, I bought (6) varieties of winter squash at once at the store because I had to have one of each. Never mind that I wasn’t sure what I was going to with all of them yet.  

The checker at the store gave me a wondering glance and asked, “What are you going to do with all this?”  I explained what I might do (which was really more like rambling), so she got more than she bargained for.  

I don’t think she’ll be asking me any more questions like that. ๐Ÿ™‚

Roasted Winter Squash in a white bowl

The inspiration for this particular recipe came from one of my favorite cookbooks, A Good Food Day by Marco Canora.   I changed up the recipe quite a bit, but it’s completely why I went this route with my beautiful squash.  If you like to eat healthy and you don’t have this cookbook, I highly recommend you pick one up!

There are so many great varieties of winter squash out there, and it can be intimidating trying to figure out what on earth to do with them, not to mention how to cut without a pumpkin carver!  

I thought I would do a nice little break down of the squash I used here, and the easiest way to cut them.

Winter Squash

Butternut squash

Prepped butternut squash

We all know and love butternut squash, don’t we?  I’d have to venture a guess and say it’s as popular as pumpkin nowadays.  It has a nutty flavor similar to pumpkin, but it’s much sweeter with a silkier texture.  It’s beautiful as a sauce, roasted, and great in dishes like soups, and chilis, and so much more.

The best way to handle butternut squash is to cut the top stem and base off with a sharp knife.  Hold it at an angle and use a vegetable peeler to remove the thick peel.  From there, lay the squash on it’s side and cut width-wise right where it starts to “blossom”.  Stand each piece upright and cut in half lengthwise from there, and scoop the seeds out of the base.  Cut each section lengthwise into 1″ slices and cube from there.

Delicata squash

delicata squash

Delicata squash is as delicious as it is pretty!  The flesh is sweet and tender — reminiscent of sweet potato.  You can roast them, stuff them, and they’re great added to a variety of salads, soups, and stews.  The best part?  You don’t have to peel them.  The peel adds great texture to the soft, silky flesh.

To cut delicata, grab a paring knife and insert it about 1″ and run it along one side, then the other.  Scoop out the seeds with a metal spoon and slice or cube.

Kabocha squash

kabocha squash

I tried kabocha squash in cooking school and it became an instant favorite of mine.  It’s basically a Japanese pumpkin, with a sweet flesh reminiscent of sweet potato, but it’s a bit starchier.  It’s great in mashed potatoes, soups, stews, chili, etc.  And like the delicata, no peeling is required!

I used to use a chef’s knife to cut kabocha squash which is a little haphazard, and read in A Good Food Day to use paring knife.  Simply lay the squash on it’s “side”, insert the paring knife into the middle widthwise to cut in half, rolling the kabocha toward you as you cut.  Pull apart, scoop out the seeds, and cut into slices or cubes.

Red Kuri squash

Red kuri squash

Red kuri was new to me until I made this dish, and I fell head over heels.  It looks like a small pumpkin without the ridges, and has a sweet flesh with a mellow, chestnut flavor.  You get to leave the peel on this one, too, and it’s magnificent anywhere you would use butternut squash or kabocha!

Cut red kuri squash the same way you would cut kabocha.

Alrighty — that concludes our breakdown.  Let’s talk about this dish a little more, shall we?

Chili Maple Roasted Winter Squash in a. bowl

The thing about this Chili Maple Roasted Winter Squash is that you don’t have to use all (4) varieties that I have.  If you don’t have time to mess with (4) different types, pick 1 or 2 favorites.  I definitely recommend using at least one with an edible skin like the delicata, kabocha, or red kuri, because of the texture it adds, as well as the color.

We do eat with our eyes after all. ๐Ÿ™‚

Bowl of roasted winter squash with a spoon

For this dish, I used half of a butternut, kabocha, and red kuri, then placed the other half of cubed squash in the freezer for another use.

The sweet and spicy flavors in this dish make it an instant keeper.  I call this spicy, but it’s not hot-spicy.  There’s just a nice warmth and depth of flavor reminiscent of a bowl of chili.  The sweetness of the squash and the maple syrup balance everything out so nicely.

The vinaigrette adds a nice little zing to the to whole thing with a punch of apple cider vinegar and dijon.  You can go ahead and garnish this with sliced green onions for freshness, or toasted pumpkin seeds for a nice crunch. However you decide to serve this up, it will be perfect for fall entertaining, Thanksgiving, or a great way to get the kids to eat some new veggies.

This dish….it’s fall in a bowl. ๐Ÿ™‚

Chili Maple Roasted Winter Squash |

Chili Maple Roasted Winter Squash

Chili Maple Roasted Winter Squash is winter squash roasted to perfection with chili powder and maple syrup, and tossed in an maple orange vinaigrette.

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For the squash:

  • 8 cups winter squash cut into 1 1/2″ cubes I used 2 cups each red kuri, kabocha, delicata, and butternut varieities*
  • 2 tablespoons extra virgin olive oil
  • 1 tablespoon maple syrup
  • 2 teaspoons chili powder
  • 1/4 teaspoon cayenne pepper

For the vinaigrette:

  • 2 tablespoons apple cider vinegar
  • 2 tablespoons fresh orange juice
  • 1 1/2 tablespoons maple syrup
  • 1 teaspoon dijon mustard
  • 3 tablespoons extra virgin olive oil
  • salt and pepper to taste


Prepare the squash:

  • Preheat the oven to 350 degrees. Toss the squash in the olive oil, maple syrup, chili powder, cayenne pepper, and salt and pepper, and spread in a single layer in a large rimmed baking sheet. Roast for 35-45 minutes or until the squash is very tender. Set aside to cool slightly.

Prepare the vinaigrette:

  • In a small bowl, whisk the vinegar, orange juice, maple syrup, and dijon mustard until combined. Add the olive in a steady stream while whisking constantly until the dressing has emulsified. Add salt and pepper to taste.
  • Place the squash in a large bowl. Add the enough of the vinaigrette to coat the squash and gently toss until combined. Serve warm and enjoy!


  • *You don’t have to use all (4) varieties of squash here — any variation will be great! Delicata, kabocha, and red kuri squash don’t require peeling, and add a wonderful texture and color. I definitely recommend using at least one of them.
  • *See my tips on the best way to cut each squash in my post.
  • Recipe inspired by the cookbook A Good Food Day by Marco Canora.


Calories: 172kcal, Carbohydrates: 23g, Protein: 2g, Fat: 9g, Saturated Fat: 1g, Polyunsaturated Fat: 8g, Sodium: 76mg, Fiber: 6g, Sugar: 11g

Nutrition is estimated using a food database and is only intended to be used as a guideline for informational purposes.

Did you try this recipe?Be sure to tag @flavorthemoments with the hashtag #flavorthemoments on Instagram so I can see what you made!

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