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Sausage Stuffed Squash with Apples & Aged Cheddar

Sausage Stuffed Squash with tart apples and aged cheddar, oh my! A cozy recipe with all the flavors for the cold days ahead.

Even squash haters will like this one, because, welp, they can technically just eat the filling and no one is the wiser. No awkward moments of not finishing your meal, because the squash is technically the bowl. And when parents say, “clean your plate,” they can’t possibly mean eat your plate.

Unless, of course, you want to eat your plate, because it’s made of squash. You can definitely do that in this case. I guess what I’m trying to say is that you have options here. Any time your food bowl is edible, I feel like you’re winning.

ingredients for stuffed squash
sausage stuffed squash dish
garden squash

Sausage-Stuffed Squash: The Details

From mini pumpkins to winter squash, tart apples, aged cheddar, and badass kale, let’s get to the sausage-stuffed squash deets. And yes, kale IS badass.

Squash, Pumpkins, & Fairy Godmothers

Stick with small- or medium-sized squash, because they’re cute. Look for fun, local varieties or grow your own! I have it on authority that fairies live in gardens, so you’ll up your odds that your pumpkin was once a princess carriage. Just sayin’.

The size of your squash will determine how long you bake before stuffing. If you go with small winter squash, like mini pumpkins, you’re looking at 20-30 minutes. If you go with medium squash, like acorns or red kuri, you’re looking 35-45 minutes.

For the record, if I had to pick a favorite squash, it would probably be red kuri. Whenever my sister and I discuss the nuances of winter squash varieties, as you do, this one is at the top of the list!


Spicy, Italian sausage. I really don’t need to say more.


Because the squash is already pretty sweet, go with a tart apple. Pink Lady and Haralson are great choices.

acorn squash garden
garden kale
cooking kale

Aged Cheddar

Go for a really old one! Not old like one that’s been in your refrigerator too long, but old like one that has been aged for five years. It really adds to the flavor here, and bonus, you have a delicious snack while cooking.

And do you know what pairs well with aged cheddar? Wine. You’re welcome.

Badass Kale

Don’t be scared of the amount of kale in this recipe, as it cooks down significantly. And eating kale makes you more badass. That’s just how it works with kale.

sausage stuffed squash with kale, apples, and cheddar
sausage stuffed kale served

Sausage Stuffed Squash with Apples & Aged Cheddar

Hearty winter squash stuffed with spicy sausage, apples, kale, and aged cheddar. A cozy recipe on repeat for the cold days ahead.
Prep Time 15 minutes
Cook Time 1 hour
Total Time 1 hour 15 minutes
Course Main Course
Servings 4


  • 4 small or 2 medium winter squash
  • 2 T olive oil divided
  • S&P
  • 2 shallots chopped
  • 2 lbs spicy, Italian sausage
  • 2 apples diced
  • 4 cups kale washed and torn into bite-size pieces
  • 2 tablespoons heavy whipping cream
  • 1.5 cups aged cheddar cheese


  • Preheat oven to 400 F. If using small squash, cut the tops off. If using medium squash, cut in half. Scoop out seeds. Brush with 1 tablespoon olive oil and season with salt and pepper. Place on baking sheet and roast for 20-45 minutes depending on size (20-30 for small; 35-45 for medium). Remove once tender and set aside until stuffing is ready.
  • Meanwhile, heat remaining 1 tablespoon olive oil in large nonstick skillet over medium heat. Add shallots and saute 2-3 minutes. Add sausage, breaking up with a wooden spoon, and cook until just browned (if there is a significant amount of fat in the pan, you could drain at this time). Add apples and kale, stirring until kale has significantly cooked down. Add cream and cheddar cheese, stirring to combine.
  • Once squash is fork tender, scoop stuffing into squash. Return to oven for 10-15 or until heated through. Enjoy!
Keyword fall, healthy
Did you make this recipe?Tag us @petalbackfarm on Instagram or leave a comment below!

Alright, what’d ya think of this Sausage Stuffed Squash? Think it sounds yummy? If so, I’d love it if you shared with your friends!

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