Stuffed Acorn Squash

Stuffed Acorn Squash with Italian Sausage: Your New Fall Go-To

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Let’s be honest—acorn squash doesn’t get the love it deserves. It’s like the underdog of the squash world, hanging out quietly while butternut and spaghetti squash hog all the attention. Write honestly, I was intimidated by it! But today, we’re going to dispel and hesitations surrounding these cute little squash with this easy and delicious ensemble.  It’s hearty, it’s flavorful, and best of all, it’s way simpler to make than you might think.

First off, let’s talk about the squash itself. Acorn squash is like nature’s ready-made bowl. You literally just cut it in half, scoop out the seeds (easy peasy), and boom—instant edible serving dish. The hardest part? Trying to slice through it without the whole thing ending up on the floor. But once you’ve got it halved, the rest is a breeze. Roast it until it’s fork-tender and caramelized around the edges, and it becomes sweet, nutty, and melt-in-your-mouth delicious.

And that’s before we even get to the filling! We’re talking savory Italian sausage, sautéed with onions, garlic, spinach for some contrasting color and most definitely a sprinkle of cheese to top it off. You just stuff all that goodness into the roasted squash halves, top with shredded cheese, pop them back in the oven for a few minutes, and voilà—a perfectly balanced, show-stopping dinner that looks way fancier than the effort it requires. Plus, acorn squash is the perfect size for individual servings, which means everyone gets their own adorable, tasty squash bowl.

So if you’ve been avoiding acorn squash because you thought it was tricky, trust me, it’s easier than you think. Let’s get cooking and turn this underrated veggie into the star of your fall menu.

I stumbled upon a recipe for stuffed acorn squash about 15 years ago in a magazine I was browsing while waiting in line at the grocery store. It sounded so delicious that I just had to try it. As with every recipe I make, it has evolved over time and now I have perfected it. I am confident that it will be a hit every time!

When making this recipe, it’s crucial to be picky when selecting your acorn squash. The size and shape of each squash are important for presentation and serving size. To ensure uniformity, choose squash that are similar in size and shape. It’s best to select round squash rather than elongated ones, as you’ll be using the halved squash as serving bowls.

Cutting acorn squash can feel like a dangerous sport, but don’t worry—I’ve got you! To avoid squash flying across the kitchen (or losing a finger), start by slicing off the pointed and stem ends. This gives you flat, stable edges to work with. Then, just cut through the middle to split it in half. Boom—two perfect squash bowls, no casualties!

Now that you have your squash prepped drizzle the inside with olive oil and give a nice dusting of salt and pepper. Flip the squash over onto a foil-covered baking sheet and back at 350 for about 20 minutes. Having the squash flipped flesh down will help steam the inside. Pull the squash out and check the flesh to make sure it is fork-tender. Flip the squash bowl side up and put back into the oven for another 10-15 minutes. This will start to crisp the inside a bit. 

MEANWHILE

The stuffing is super simple and therefore super easy! Start with a rough chopped medium yellow onion. Sauté until translucent. Add 1 lb of bulk Italian sausage. Brown until it starts to crisp a bit. Add 1/4 cup chicken stock & 1/4 cup white cooking wine. Throw in 1 inch cubed sourdough bread cubes and toss. Let the bread soak up the juices a bit. Add 1 cup fresh spinach. Toss until the spinach wilts.

Pull the squash out of the oven and fill the bowls with stuffing. Stuff generously. Top with shredded gruyere and place back in the oven and broil until the cheese melts and starts to bubble.

Pull out of the oven and drizzle with balsamic vinegar. Trust me on this- DO NOT SKIP THIS STEP. It adds an incredible sweetness that compliments the salty savory flavors in the squash and stuffing.