This is the first time I’ve made any kind of stuffed squash, and I LOVED IT! More than I expected honestly.  I like chili and I like squash, so I figured I’d like it just fine.  But I didn’t expect to feel like these two were always meant to be together! I’ve decided I think it’s because the sweet delicata kind of replicates sweet cornbread for me. And I could marry cornbread. (LOVE). The less healthy and more like straight up yellow cake (ahem – Trader Joe’s boxed mix) the better.  Yep.

Maple Roasted Stuffed Delicata Squash with leftover chicken chili

Since I’d roasted the squash with a little Walden Farms syrup, it didn’t seem too crazy to drizzle a little more on, right over the chili. OH MY GOSH what has gotten into me. I’m starting to think everything might be better with syrup. SO good.  I didn’t have that (um genius) thought until after I snapped these photos or I would have made sure you could see it to drool over it.

Ok have I mentioned though that I’m really into sweet and salt?   Syrup on my chili and flake salt on my ice cream please.  If you’re one of those that keeps your savories and sweets in different corners of the ring then maybe it’s not for you– WHATEVER.

Maple Roasted Stuffed Delicata Squash with leftover chicken chili

I love meals that can come out of the oven on a sheet pan all at the same time.  And this is so quick and easy because of the leftover chili!  As my kids get older, our lives just keep getting BUSIER, and I’ve just learned that cooking large batches of things that I can repurpose later is a MUST.  I used to think leftovers were garbage, but there are so many things that can be just as good or better if done right on round two, three, or more!

Soup and chili make pretty good leftovers on their own.  No risk of reheated meat flavor really…  But even still, sometimes you just don’t want to have the exact same meal twice in a week. This was the perfect way to use our leftover soup (that by round two was extra thick and more like chili anyway).

So quick and healthy and delicious.  And now I can’t stop imagining all the things that would be good stuffed in these gorgeous little delicata gems and drizzled with syrup…. hmmmm

Maple Roasted Stuffed Delicata Squash with leftover chicken chili
Maple Roasted Stuffed Delicata Squash with leftover chicken chili

Maple Roasted Chili Stuffed Delicata Squash

A perfect cozy fall meal using leftover soup or chili.  I paired mine with a simple kale salad for just a handful of additional carbs.
Author Lillie
Prep Time 10 minutes
Cook Time 25 minutes
Servings 1
Calories 463 kcal


  • 1 whole delicata squash- found at Trader Joes and most stores right now (380g)
  • 1 cup Leftover chili- I used this instant pot chicken tortilla soup/chili (240g)
  • 1 Tbsp. Lite shredded 3 cheese blend (15g) I like the one from Trader Joes
  • 1/4 Avocado (30g)
  • 2 Tbsp. Cilantro
  • 1 Tbsp. Favorite low or no sugar maple syrup I like Birch Benders Magic Syrup


  • Cut the squash in half lengthwise and scoop out the seeds with an ice cream scoop
  • Spray with olive oil spray and sprinkle liberally with kosher salt and pepper
  • Drizzle maple syrup over the top
  • Place cut side down on a parchment lined baking sheet
  • Roast at 400 for about 20 minutes
  • Take out, flip, fill with chili and top with 7 g cheese per half
  • Bake for another 5 minutes just until cheese is melted
  • Top with avocado, cilantro and another little drizzle of syrup (sounds weird but I’m obsessed.)


When I’ve cut the squash like this recipe, the skin turns out so tender and is one of my favorite things about the delicata! This time there were parts of my skin that were too tough so I scooped it out instead. But if yours is tender enough, you can cut through and eat the whole thing. If not, be sure and weigh the skin that’s left to subtract it from your squash macros.


Serving: 2stuffed halvesCalories: 463kcalCarbohydrates: 69gFat: 8gSaturated Fat: 2g

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About the Author

Hello. My name is Lillie. I’m not a registered dietitian, or a macro coach, or a public figure or culinary genius. I’m a mommy of four who FOUND macro-counting and fell in love with this balanced approach to food...

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