Chili Maple Roasted Winter Squash
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!
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. 🙂
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.
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 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
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 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?
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. 🙂
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. 🙂
Chili Maple Roasted Winter Squash
Ingredients
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
Instructions
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!
Notes
- *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.
Nutrition
Nutrition is estimated using a food database and is only intended to be used as a guideline for informational purposes.
45 Comments on “Chili Maple Roasted Winter Squash”
This is a great post Marcie! I’m not familiar with many of the other kinds of squash, so this was really helpful! I will definitely have to get a little braver and experiment some more 🙂
I’m glad you found it helpful, Ashley! There are so many delicious varieties of squash I can never decide on just 1 or 2!
Wow I actually didn’t know there were that many different types of winter squash! I’m so glad that fall is here officially too so that I can start cooking with it. This squash sounds fantastic, Marcie! I absolutely love the flavors that you paired it with. Sounds like the perfect side dish for the season!
There are even more varieties than what I listed here — this could be part 1 of 2! haha Winter squash makes me so excited for fall. 🙂 Thanks, Gayle, and hope you’re having a great week!
I could eat just this all Fall and Winter long, looks so good!
You and me both, Matt! Thanks, and have a great rest of the week! 🙂
Dear Marcie, I love winter squash. This dish is beautiful and sounds absolutely delightful. I love the flavors…I can only imagine how wonderful it is. Such a perfect blend of ingredients. xo, Catherine
Thank you, Catherine! This was worth the effort to cube all the squash — it’s such a great fall experience. 🙂
Whoa! You are the queen of all things squash, Marcie! LOVE your guide to winter squash—definitely gonna use this one because seriously, ANY kind of winter squash is my jam come fall!
Haha! You crack me up. 🙂 I wanted to include so many other varieties but there are too many for one post. So much squash, so little time. To be continued…:)
Yay for Fall!!! We will be eating this a ton this year! It looks amazing!
Thanks so much, Annie! We’ll be eating it a lot, too! 🙂
My mouth is watering over this gorgeous bowl of squash. I love roasted winter squash and can eat it everyday for lunch and dinner. This is such a helpful guide too – I’ve never tried red kuri before so I can’t wait to look out for it next time. Love the sweet maple and spicy chili flavors!
Thanks so much, Kelly! I read about red kuri in the cookbook I mentioned in the post and had to grab one. It was delicious! 🙂
This is such an awesome post, Marcie! Beautiful and delicious. I can eat this for all my meals. Can’t wait to try. Yay for Fall!!!
Thank you, Anu! I see a lot of squash in my meals this fall/winter. 🙂
Sometimes it is better when the checkout people don’t ask too many questions, haha! That is great that you bought one of each! I love roasting squash and that chili maple flavor sounds so good!
I know, I think the checker might have been sorry she asked! haha Thanks, Izzy! 🙂
I love that you took the time to explain the different types of squash! I remember feeling so intimidated by all of it when I first started cooking. And I still haven’t tried many of them, like the red kuri. I’ll have to keep an eye out so I can try it roasted like this. That orange maple vinaigrette paired with the chili powder sounds out of this world!!
Thank you, Sarah! I had no idea you could leave the peel on kabocha squash when I made it and always peeled the whole thing. haha The peel is such a delicious part of it! Hope you find that red kuri. 🙂
I love acorn squash, too — there are so many delicious varieties! I’m with you…I missed it very much. 🙂
Normally I only roast the squash in the chili powder and maple, but the cookbook I mentioned inspired me to make a vinaigrette. Was it ever tasty! The edible skin is such a time saver, it’s so pretty, and the texture is adds so much. 🙂
Thanks, Kennedy! And I appreciate the pin! 🙂
I DREAM about winter squash, DREAM ABOUT IT! I am obsessed, beyond obsessed – LOL! You are making me drool ridiculously TOO MUCH! lol
Sounds like we have the same dreams! Well, one anyway. 🙂 Thanks, Gigi!
I love butternut squash, but haven’t tried the others in this dish. You’re totally inspiring me to try some though, because this looks delicious!
The peel on the other squashes really adds so much! I hope you try them, Danielle! 🙂
I have never cooked with ANY kind of squash before! This is a great post!
Thanks so much, Cathleen! I hope you get to try it this fall/winter! 🙂
This is absolutely lovely, Marcie, from the colours in the dish of squash to that wonderful vinaigrette! I always find it difficult to peel butternut squash, too, so thanks for the tutorial!
Thank you, Helen! Hope you had a great a weekend!
Oh thanks for the breakdown. I’m usually only eating butternut and delicata but I should explore more. And this whole sweet and spicy going on here is just wonderful!!
Thanks, Z! I’m so glad I got around to trying red kuri squash…I had no idea what I was missing. 🙂
haha I definitely get wayyyy too excited when I start seeing all the squash in the store!! This dish sounds absolutely fantastic Marcie – cannot wait to try it out! And that vinaigrette!!
I got a little bit overexcited when I saw all the squash but it was so worth it! Thanks, Ashley! 🙂
Love the combination of all these different kinds of squash! Looks perfect! Meals like this are one of my favorite things about fall -colorful and delicious ! Pinned!
Thank you, Mira, and I appreciate the pin!
I am a squash un-aficionado so I totally needed this Marcie. Thanks for the great information and delicious recipe!
I’m glad you found this informative, Trish! Thanks, and happy Monday! 🙂
This looks sooo good!! Love the chili and maple on there, and thank you for the how to cut photos! I have no idea how to do it, haha. Pinned!
Before I knew how, cutting squash was a scary thing! haha Thanks for the pin, Rachael! 🙂
I love the guide to these winter squashes. I do not know about some of them!
I’m glad you found it helpful, Nancy!
I love the sweet & spicy flavors of this dish – sounds so delicious!
Thank you, Cathy!