This Roasted Stuffed Acorn Squash is filled with all your favorites – sausage, apples, cranberries, onions, celery and savory herbs. The stuffing is packed with savory/sweet flavors and the perfect addition to a holiday gathering, or for any meal! Paleo, gluten free, Whole30 compliant.
I’ll just come right out and say it – stuffed acorn squash is one of my most favorite foods OF ALL TIME.
Seriously, if you had told me just five years ago that I’d make such a statement, I would’ve been pretty darn confused, given that back then, I didn’t even know what an acorn squash WAS, let alone how/why/with what I’d be stuffing it.
So, hopefully many of you are already far more enlightened than I was back then, but if not, no worries at all! You’re in for quite the (Paleo & Whole30) treat. Meet your new best friend – the acorn squash – shown above.
The name comes from its shape, and trust me, the inside tastes way better than it sounds, especially after being roasted.
To be brutally honest with you, I love it more than butternut squash. Plus, I find acorn squash easier to prepare – they’re not at all the hassle that butternut can be, making them a pleasure to work with, and then of course, to eat.
Now, like magic, after roasting your acorn squash and stuffing it with, um, basically ANYTHING, it becomes downright addicting.
Seriously, forget the chocolate and treats – this is the real paleo crack – roasted and stuffed acorn squash.
You might remember me saying the same thing about last year’s caramelized onion, sausage, apple and spinach stuffed squash. Well, this one is just a touch on the sweeter side – with fruit-sweetened cranberries (holla!) toasted chopped pecans, and no spinach, but MAN! You can’t really go wrong when you stuff an acorn squash.
No doubt that after trying it (and seeing for yourself how easy it is!) you’ll begin a lifelong acorn squash hoarding problem, like I’ve had for 3 years now.
September comes and I just can’t say no when I see all the squash at the store! Which is why I have quite a few hanging around in bowls all over the place. My kids don’t know if they’re food or decor.
And, I haven’t even begun to address my delicata problem yet. More on that one next week!
Okay here’s the deal – you roast the squash first. It only takes about 30 minutes, just enough time to get all your filling prepared.
Chop the veggies and herbs, cook the filling on the stovetop, stuff the squash, then broil for a few minutes until you get a nice “crisp” texture on the stuffing and around the edges of the squash.
Then, voila – the most delicious thing you might eat for a very long time. Or, at least until the next time you roast acorn squash.
Now, you might be wondering what to serve this with, and the answer, is that it’s completely up to you!
You can absolutely serve this as a holiday side dish – as a side – it will serve about 8 people, though you’ll have to cut the squash halves in half, or just have people dig in and scoop their portion right out of the squash.
As for me, I literally can’t stop eating it once I start, so, it works better as a meal. I’d say the recipe will serve 4 as a full meal.
You can also prepare the squash and stuffing ahead of time, so all you have to do is the stuffing/broiling step prior to serving. And, if you wish to make the entire thing ahead of time, you can definitely reheat the finished product in the oven with almost no change in texture/flavor. I did exactly that 3 times last week after taking the photos 🙂
I hope you’re ready to get cooking, because this one is going to knock your socks/headband/oven-mitt right off. Let’s go!
Stuffed Acorn Squash with Sausage, Apples and Cranberries {Paleo, Whole30}
Stuffed Acorn Squash with Sausage Apples and Cranberries {Paleo, Whole30}
Ingredients
- 2 small/med acorn squash
- 1 tsp organic coconut oil or ghee, plus sea salt, for roasting
- 1 Tbsp organic coconut oil or ghee, plus more, if needed
- 1 lb pork sausage bulk, sugar-free for Whole30
- 1 small onion diced
- 2 celery stalks diced
- 2 cloves garlic minced
- 1 small apple diced (pink lady is my favorite for cooking)
- 1 Tbsp fresh sage leaves minced**
- 1 Tbsp fresh rosemary leaves minced**
- 1 Tbsp fresh thyme leaves minced**
- 1/3 cup dried cranberries fruit-sweetened for Whole30
- 1/3 cup raw pecans chopped, toasted prior to adding, if desired
- sea salt and pepper to taste
- fresh parsley for garnish if desired
Instructions
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First, roast the squash. Preheat your oven to 425 degrees F and line a large baking sheet with foil or parchment paper.
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Cut each squash open, lengthwise, the scoop out the seeds/strings with a spoon, leaving a “bowl” in the center.
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Brush the top of each squash half with melted coconut oil (or ghee) and sprinkle lightly with sea salt, then place face down on prepared baking sheet, and roast for 25-30 minutes, or until top of the squash feels soft when you press on it.
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Roasting time will vary depending on the size of your squash. You can remove, check for doneness (it should be soft enough to eat) and return the the oven for a few more minutes if necessary.
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While the squash roasts, prepare the stuffing. Heat a med/large skillet over med-hi heat and add a Tbsp coconut oil or ghee to melt. Add your sausage, breaking up lumps with a wooden spoon to evenly brown. Once browned, remove from heat and transfer to a plate, leaving fat in the skillet.
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Return skillet to medium heat and add the onions and celery, stirring while cooking to soften, about 3 minutes. Add the garlic and cook another minute, stirring to avoid browning.
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Add the diced apples, fresh herbs and salt and pepper to taste, stir to combine. Cook for another 1-2 minutes to allow apples to soften.
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Then add the cranberries, pecans, plus browned sausage back to the skillet, lower heat to med/low and continue to cook another 2 minutes to blend flavors.
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Once ready to stuff the squash, preheat your broiler and arrange the 4 squash halves face-up on the baking sheet. Scoop the stuffing mixture into each one, adding as much as you want to each. You might have leftover stuffing depending on how large your squash are and how much you fill them.
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Once filled, place the baking sheet under the broiler and broil until tops of stuffing and squash are nicely browned, 5 minutes or so. Garnish with fresh minced parsley, serve and enjoy!
Recipe Notes
**Use 1 tsp each if using dried herbs
***You can make the stuffing and roast the squash ahead of time, then simply fill and broil at the last minute for a quick meal!
Nutrition
What I Used To Make My Stuffed Acorn Squash:
Want More Paleo and Whole30 Winter Squash Recipes? Try one of these!
Butternut Sausage Apple Cranberry Thanksgiving Stuffing
Roasted Butternut Squash Hash with Apples and Bacon
Acorn Squash with Caramelized Onion Sausage Stuffing
Butternut Squash Fries with Bacon and Rosemary
Tell Me!
What do you HAVE to buy when you see it at the grocery store?
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This recipe is fall comfort food at its finest! The balance of savory sausage with the sweetness of apples and cranberries is absolute magic, and the acorn squash makes the perfect edible bowl. I love that it’s Whole30 and paleo-friendly without sacrificing flavor—definitely going into my seasonal dinner rotation.
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This recipe sounds absolutely incredible! The combination of sausage, apples, cranberries, and savory herbs tucked into roasted acorn squash feels like the perfect balance of comfort and elegance. I love how it’s not only packed with flavor but also Paleo, gluten-free, and Whole30 friendly — such a win for holiday gatherings where everyone has different preferences. Definitely adding this to my fall cooking list!
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