Nourishing Tummies (Recipes)

Caramelized Onion and Apple Stuffed Acorn Squash

It’s official: fall is my very favorite season in the kitchen.

This fall marks a year since we started our local/seasonal produce endeavor. Through this year, I’ve stretched myself in the kitchen to work through the offerings of each. I can confidently say that fall is now my very favorite season.

If you haven’t guessed, there’s a very good reason behind this: I love fall squashes (summer squash, not so much). Of course, I love pumpkin – who doesn’t?! But pumpkins are rather unwieldy. It takes a lot of work to get through one of the 20+ pound monsters I pick up. Often, I relegate pumpkin prep to the weekends.

Thankfully, pumpkin is hardly the only squash available in autumn. Spaghetti, butternut, delicata, patty pan and acorn squashes dominate the season – and they’re perfect for weeknight dishes.

Working With Squashes

There are a lot of things to do with squashes – if you know your way around some basic ingredients and a sharp knife, that is. Many people avoid squash or limit its potential simply because they’re unfamiliar with preparing them.

Fear not! Today, we’re going to add a new, delicious recipe to your squashy arsenal. Impress your spouse. Impress your friends. Whatever you do, hop on down to the farmer’s market and grab a basket of acorn squashes ASAP!

When working with fall squashes, it’s important to remember two things. 1) You need to get through the thick skin in order to get to the good stuff. 2) You need to give your squash plenty of time to cook.

While there are some exceptions, a general rule with fall (and winter) squashes is that you want to cook them for a good long time and worry about removing the skins only after they’re fully cooked. Your patience is rewarded. Instead of having plain old squash mush when you pull something out of the oven, you instead get lovely little presentation boats.

And that brings us to today’s main topic:

Caramelized Onion and Apple Squash Boats

Last fall, I had a newborn and I wasn’t much for putzing around with new recipes in the kitchen. I was also still working mornings at my old office job, so often I’d end up having lunch at my mom’s when I went to pick the kids up. Throughout the fall, she was kind of on a stuffed squash kick, and her go-to recipe involved sausage and rice.

I. Love. Sausage. (Haha.) I’m German, so it’s only right. Stuffed squashes with sausage are my jam, but since we’ve moved away from most processed food (even my beloved farm fresh sausages), I try not to rely on it when I’m planning my weekly menus.

I knew that this fall I’d want a solid stuffed squash recipe to rely on, but I need one that’s veggie centric, rather than sausage centric. Again, while sausage is fine and good, it’s simply not a staple around here.

And thus, my caramelized onion and apple squash boats were born.

Fair warning, this is a recipe that takes over an hour to prepare. Not much of the process is active, but you do need to be present to make sure things cook properly. So pour yourself a glass of wine and settle in for some dinner prep.

First Steps

There are two things you’ll want to do right away. First, halve your acorn squashes, slather them with a bit of olive oil, and put them face down in a baking dish. I used two squashes, halved, to feed Josh, myself, and the kids – and we still have some leftover.

Cook the squashes at 375 for 45 minutes to an hour or longer. The cook time is highly dependent on squash freshness and skin thickness. Mine took maybe 45 minutes to cook this time, but I’ve had stubborn acorn squashes that have taken up to an hour and a half to cook.

While the squashes cook, you can start working on the filling. As our recipe title indicates, the filling is comprised largely of caramelized onions, which do take a while to make. Since you’re already working on the squash, you have the luxury to get your onions going without trying to rush them into another part of the recipe, so take a medium onion or two, cut them into slices, and stick them into a pan over low heat with some butter and salt. Let those cook up for 30-40 minutes, or until they basically fall apart and caramelize.

Even as the other components are cooking, you can also go ahead and cook up a cup or so of wild rice – this will likely take longer than an equivalent amount of white or brown rice, so consult your package for exact timing and proportions. Hey look, you’re dinner is practically cooking itself!

Yet again, while everything is cooking itself, go ahead and cut up an apple, a package of mushrooms, and half a cup of walnuts. Just use whatever produce you have on hand. When I made this recipe, I used a Honeycrisp apple and a package of baby portobello mushrooms. If you’re seriously averse to one of the ingredients, like mushrooms, you can simply leave them out without noticing a huge difference.

Caramelizing Apples

Now, you’ll notice that these stuffed squashes are comprised of caramelized onions and apples. I know what you’re thinking: do these contain caramelized onions… and apples? Or caramelized onions and caramelized apples?

These stuffed squashes do actually contain caramelized apples. Never caramelized an apple? Not to worry! Here’s what to do.

After your onions have cooked down for 15 to 20 minutes or so, toss your diced apple in with them. And that’s about it!

Apples are far fleshier than onions, so they don’t require as much time to cook down as fibrous onions do. Be sure to add some extra salt, and perhaps a bit of extra butter if you feel your pan needs it. Then let them simmer together while your squashes finish cooking. That’s all there is to it!

After your onions and apples have cooked down for about 10 minutes together, go ahead and add your mushrooms, since they’ll only take about five or so minutes to cook down. When your wild rice finishes cooking, add this to the mixture too.

At this point, your stuffing mixture is nearly together, so add your walnuts and seasonings. As far as seasonings go, I tend to get a little abstract in this department. For the mix, I used some typical fall spices, like nutmeg, cinnamon, cardamom, and allspice. I also used some of my favorite savory spices, including paprika, coriander, and cayenne. Once you’ve settled the spice question, your squashes will probably be close to ready.

Putting it All Together

With the squashes cooked and your mixture prepared, it’s time to marry the two and call the family to the table. Simply heap your squash halves with as much filling as you and your family members will appreciate. I scooped a bit of the acorn squash guts (ew, sorry) out of the middle to make a bit more room for filling, and I recommend that you do the same. I also added a touch of shredded white cheddar over top of each stuffed squash and popped them under the broiler for a few minutes.

And there you go! A lovely fall dinner that everyone will love. Even my kids ate the squash – about a quarter apiece. I’ve already got these babies slated for an upcoming dinner, and I have a feeling we’ll actually be sick of them by the time fall is over. That’s a risk I’m willing to take!

Caramelized Onion and Apple Stuffed Squash
Total Time
1 hr

Welcome fall with a lovely mix of fall veggies in this classic vegetarian staple dish!

Course: Main Course
Cuisine: Gluten Free, Vegetarian
Servings: 4
Author: Gabrielle Rystedt
  • 2 Acorn Squashes lightly oiled
  • 1 cup Wild Rice
  • 1 large Onion (or 2 smaller ones)
  • 1 Honeycrisp Apple
  • 1 package Mushrooms
  • 1/2 cup Walnuts
  • 3 tbsp Butter
  • 1 tbsp Paprika
  • 1 tsp Nutmeg
  • 1/2 tsp Cinnamon
  • 1/2 tsp Cardamom
  • 1/2 tsp Coriander
  • 1/2 tsp Cayenne
  • 1/2 tsp Black Pepper
  • 1/2 tsp Allspice
  • 1 tbsp Apple Cider Vinegar
  • 2 oz Shredded Cheese (optional)
  1. Bake the squashes: Preheat oven to 400F. Meanwhile, half your squashes, deseed them, and place them face down in a rimmed baking dish. You may lightly oil them if you desire.

  2. Caramelize your onions: Slice your onion(s) into thin slices and add them to a hot pan with 2 tbsp of butter and a generous sprinkling of salt.

  3. Prepare wild rice in a separate pot according to package directions.

  4. Caramelize your apples: after the onions have cooked down for 15-20 minutes, add your diced apple and some extra butter and salt, if you desire.

  5. Finish the mix: add cut up mushrooms, walnuts, wild rice, AC vinegar, and all spices to the mixture and let cook down for five or so minutes. Adjust any seasonings to your taste and add any extra salt.

  6. Prepare the squashes: Once the squashes have finished baking and are fork tender, remove them from the oven, turn them right side up, and remove a little of the middle bit from each squash.

  7. Stuff the squashes: Add mixture to each squash half to your taste. Sprinkle with shredded cheese, if you wish, and broil for an additional two or three minutes.

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Gabrielle Rystedt
Gabrielle Rystedt
Gabrielle Rystedt is a writer by day and a writer by night (because writers never sleep), who spends time balancing client orders, a couple of books and her blog at Raising Rystedts. She’s a business school grad who’s dabbled in management, both at the project and company level. She loves coffee and crafting, and enjoys settling down with a good book. Though as mom to three kiddos in three years, she realistically spends most of her time reheating her coffee and typing away like a crazy person on a laptop keyboard while surrounded by (clean) cloth diapers and cheddar bunnies.

What are your thoughts?