Stuffed Acorn Squash

Who doesn’t love stuffing things inside of other things? I feel like certain foods kind of beg us to do this. Why do butternut squashes have huge holes in them? Why do peppers look so darn cute when stuffed with ground beef and topped with their little pepper tops? Why do we insist on double-stuffing baked potatoes with all sorts of extras and calling them “twice baked”? I don’t know, but I’m happy to do as I’m told here. Food stuffed with more food? It definitely keeps things interesting.

You know what else is really interesting? Acorn squash. No joke, I’m sort of in love with it. Well, now that I actually figured out how to cook the suckers, I’m in love with them. Come to think of it, “love” might be a very strong word and I’m not entirely sure I’m ready to take that step so early in our seasonal relationship. So, let’s just say I’m in like with it.

The key to cooking acorn squash (for me) is to really leave it in the oven for an hour….a good hour. You might even need longer than an hour, so don’t plan on this stuff being ready inside of 45 minutes on a Tuesday night (ahem…lesson learned). In fact, my mother sent me a link to an Eatocracy article outlining just how the heck you cook the darn stuff anyway. Very helpful information in there, and it even breaks down the suggested methods according to squash variety. Ooohhhhh…..

Before I get into that, filling is fun, so let me show you what I threw together.

Stuffed Acorn Squash

Sweet potatoes and….yes, reader, that is in fact…kale. I have so much of the stuff left over from last week, I just needed to use it up. Feeling comfortable enough that I could manage a pan saute (and because I figured it wouldn’t hurt anyone being mixed in with sweet potatoes), I threw it in there along with some onion and pistachios. Fun! A word on finely diced sweet potatoes…

Stuffed Acorn Squash

Have patience, grasshopper, for cubing up these puppies into a 1/4-inch dice is a HUGE pain in the tuchus. But, the end result is so much fun and really rewarding. I like my starches clearly defined and geometrical. I think they taste better. :-) Now, I probably went about this the complete opposite way any other stuffed acorn squash recipe would tell you to do this. I cooked the dickens out of the squash first, then I spooned the filling into the squash and brought it all up to temp in the oven for about 5 minutes or so until everything was hot and ready to eat. I’m sure most traditional recipes have you cook the filling in the squash, but I was so paranoid and worried about my squash not being cooked, I felt I could only really focus on one task at a time. Imagine you have two children, aged 4 and 14, both of whom need to cross the street. The 14 year old can manage on its own and doesn’t need much help. The 4 year old warrants mama’s eagle eye to make sure it crosses safely.

Yes, I did just compare my acorn squash to a 4 year old. I recognize I may need help, but more to the point, I needed to babysit the squash so I could ensure it was cooked through. You get me? Nope? Right…

Stuffed Acorn Squash

The end result was really nifty, though! Well worth the babysitting. And if you follow the suggestions outlined in the Eatocracy article, your squash will be A-OK. Here’s what I did:

1) Use a fork to poke holes all over the inside and outside of the squash.

2) Pour 1/4 cup of water in the bottom of the baking dish before you put the squash in the oven.

3) Coat the cut side of the acorn squash with fat. I used extra virgin olive oil.

These steps worked for me, and I hope they work for you, too, because then you can make this big ol’ harvest bowl of acorn squash love! Mmhhmmm…


Stuffed Acorn Squash

Prep Time: 30 minutes

Cook Time: 2 hours

Total Time: 2 hours, 30 minutes

Serving Size: 4

Stuffed Acorn Squash

An all-in-one Fall harvest bowl! This stuffed acorn squash is jam packed with sweet potato, kale, and pistachios for a sweet, crunchy, and incredibly filling vegetarian meal.


  • 2 acorn squash, halved with seeds removed
  • 1 sweet potato, peeled and cut into a 1/4-inch dice
  • 1/2 sweet onion, chopped
  • 1 packed cup kale, chopped
  • 1/4 cup plus 1-2 tbsps extra virgin olive oil
  • 1/4 cup shelled unsalted pistachios
  • 1/2 tsp kosher salt
  • 1/4 tsp freshly ground black pepper
  • 1/4 tsp dried thyme


  1. Preheat the oven to 400 degrees.
  2. Using a fork, evenly poke holes in both sides of the acorn squash (skin side and cut side). Coat the cut side of each squash evenly with 1-2 tbsps of extra virgin olive oil.
  3. In a baking dish large enough to hold all the squash, pour 1/4 cup of water into the bottom. Place the squash on top of the water and bake for about 1 hour until fork tender, but not mushy.
  4. When there's about 30 minutes left for the squash to cook, fill a large pot half way with water and bring it to a boil. Add the sweet potato and boil until tender, about 5-8 minutes. When tender, drain and set aside.
  5. Meanwhile, heat the remaining 1/4 cup of olive oil in a large saute pan on medium heat until it ripples. Add the onions and kale and cook for 10-15 minutes, stirring frequently, until onions are soft but not brown, and kale is cooked/sort of crispy. Fold in the sweet potatoes, pistachios, thyme, salt, and pepper. Check for seasoning and adjust accordingly.
  6. When the squash are done, divide the filling evenly into each half. Put the squash back into the oven for 5-8 minutes, until everything is heated through. Serve immediately.

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