Chili Stuffed Acorn Squash

Move over, chili in a bread bowl, there’s a better idea in town – Chili Stuffed Acorn Squash! You get all the fun of digging your favorite chili out of an edible bowl, only this version is veggie-packed and naturally gluten free. Plus, the sweetness of the roasted acorn squash is irresistible with spicy flavor, making this a hearty and tasty dinner for a cold night.
Love this idea? Then try Italian Ground Beef Stuffed Acorn Squash!

Delicious Details
- Cuisine Inspiration: American
- Primary Cooking Method: Oven
- Dietary Info: Gluten-free, Dairy-free option
- Skill Level: Easy
Of course, stuffing one of your favorite chili recipes inside a gluten free bread bowl is the epitome of comfort food. But prepare to be blown away when your hearty, smoky, and spicy chili is balanced with the tender, subtly sweet, earthy flavor of roasted acorn squash. Chili Stuffed Acorn Squash is the combo you never knew you needed, and you won’t believe how fun and tasty it is to enjoy this veggie-packed chili bowl you can eat!
What You’ll Need for Chili Stuffed Acorn Squash
Here’s a quick overview of the ingredients and options to make this recipe. Just below is the full recipe card with ingredient amounts and step-by-step instructions.
- Acorn Squash. You’ll need one squash for every two servings. Just cut it in half, lightly coat it with olive oil, salt, and pepper, then toss it in the oven.
- Chili. I like to make these acorn squash chili bowls after I’ve made a big pot of the World’s Best Chili because it makes so much that I always have leftovers. But if you need to whip up something fast, try my Quick Ground Turkey Chili. You can also make No-Bean Chili, or pop some Slow Cooker Hawaiian Chili in your crockpot in the morning. Also, feel free to use your favorite recipe or, in a pinch, canned chili – there are several brands that are gluten free if that’s a concern for you.
- Cheese. I always like to pop my squash back in the oven with a topping of shredded sharp cheddar to let it melt. You can use your favorite, like pepper Jack or even some cheese sauce. Also, feel free to omit it for a dairy free dish.
- Toppings. This is where you can get creative. I’m partial to sour cream or Greek yogurt and avocado. But many folks also like raw onion, cilantro, tortilla chips, and more!

Make it a Meal
- Have some bread. If you just can’t have your chili without a carby side, then bake some Gluten Free Cornbread, or whip up garlicky Gluten Free Texas Toast.
- Toss a salad. Combine your favorite greens and veggies with a drizzle of BBQ Ranch Dressing or Red Wine Vinaigrette.
- Serve with slaw. Whether on the side or on top, a crisp, cool coleslaw is a nice contrast, so try a scoop of Taco Slaw or Pineapple Coleslaw.
More Stuffed Veggie Recipes

Chili Stuffed Acorn Squash
Ingredients
- 2 large acorn squash
- 1 tsp olive oil
- salt and pepper
- your favorite chili (about 4 cups)
- 1 cup shredded cheddar cheese (about 4 oz.)
- sour cream or Greek yogurt, avocado, tortilla chips, or your favorite chili toppings
Instructions
- Preheat oven to 400°F. Coat a baking sheet with olive oil; set aside.
- Cut 2 large acorn squash in half, then scoop out and discard the seeds. Brush the cut halves with 1 tsp olive oil, then sprinkle with salt and pepper. Roast the squash cut side down until tender, about 20-25 minutes.
- Fill each squash half with your favorite chili, about 1 cup in each, and top with 1 cup shredded cheddar cheese. Return to the oven for 5-7 minutes, or until cheese is melted and slightly browned.
- Serve with sour cream or Greek yogurt, avocado, tortilla chips, or any other toppings, as desired.




This looks like the ultimate comfort food! Thanks for linking up at Best of the Weekend!
This is the ultimate comfort food. I absolutely love this dish. Pinned.
What a super fun way to serve chili in the squash, I love the added vegetable to it. My family will love this!
The kids had fun with it!