Stuffed Winter Squash

Stuffed winter squash takes many forms, including this healthy and tasty stuffed acorn squash with quinoa that you can easily make vegetarian.

A casserole dish with four halves of roasted winter squash filled with cheese-topped stuffing

Once you experience this stuffed winter squash recipe, you’re probably going to wonder how you ever made it through winter squash season without it. That’s not just because of how comfortingly tasty it is or because it’s also insanely healthy or that you can make it vegetarian for those who are so inclined. It’s also because of the nearly incalculable number of iterations you could create based on this basic recipe, depending on whatever leftovers you happen to have languishing in your fridge. As the brilliant soul who created this recipe says, you can use last night’s leftover cooked grains, sad apples that came back in the lunch box, even old corn bread—they all find their home here, she promises “most combinations of grain, green, apple, and meat work perfectly,” is her almost audacious claim. Honestly? We couldn’t agree more.–Renee Schettler Rossi

Stuffed Winter Squash Recipe

  • Quick Glance
  • 45 M
  • 1 H, 30 M
  • Serves 4

Ingredients

  • 2 acorn, delicata, dumpling, or carnival squash, cut in half through the stem and seeded
  • 2 teaspoons olive oil, plus more for the squash and dish
  • 3/4 teaspoon kosher salt
  • 6 ounces chorizo or sweet sausage, crumbled or cut into small pieces
  • 1 cup chopped leeks (2 small leeks)
  • 1 cup chopped apple (1 to 2 apples)
  • Freshly ground black pepper
  • 2 cups tender greens (spinach, tatsoi, kale, Swiss chard), stems removed and leaves thinly sliced crosswise into ribbons
  • 4 fresh sage leaves, coarsely chopped
  • 2 cups cooked millet, rice, or quinoa
  • 1/2 cup finely grated Parmesan or Cheddar cheese (optional)

Directions

  • 1. Preheat the oven to 375° F.
  • 2. Rub the cut side of each squash half with olive oil, and oil an ovenproof dish or baking sheet. Sprinkle the whole baking dish with 1/2 teaspoon of the salt. Lay the squash, cut side down, in the dish and bake until it’s very tender when pricked with a fork, 30 to 40 minutes. Remove the squash from the oven and increase the oven temperature to 425°F.
  • 3. Meanwhile, heat the remaining olive oil in a large skillet over medium heat. Add the chorizo and fry until browned. Remove from the pan and set aside. Add the leeks to the hot oil and cook until soft, about 3 minutes. Add the apple, remaining 1/4 teaspoon salt, and pepper, and cook for another minute. Add the greens and cook until sorta wilted and softened, about 2 minutes. Add the sage, cooked grains, and reserved chorizo. Cook for another minute, stirring to combine, and remove from heat. Taste, and adjust the salt and pepper, if needed.
  • 4. Turn the cooked squash over in the baking dish so it’s cut side up. (Be careful as steam will escape when you turn the squash.) Scoop the filling into the cavity of each squash half, piling it into a mountain so that it holds as much as possible. If desired, sprinkle with the cheese. Bake until everything is warmed through, about 15 minutes. Serve warm.

Variations

  • Crumbled crisp fried bacon (about 4 strips) is a great substitute for the chorizo.
  • Crumbled corn bread is a delicious substitute for the grain. When you make corn bread and have a few pieces left over, crumble them and freeze them.
  • If you don’t have leeks, substitute a medium red onion or a couple shallots.
  • If you don’t have Cheddar, substitute Parmesan or other sharp cheese.
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Recipe Testers Reviews

This stuffed winter squash dish had all the bounty of fall in one neat package– hearty grains, smoky bacon, earthy greens, sweet apple, mellow squash. I used acorn squash and it made for a pretty presentation and was almost a meal in itself. I roasted a pork tenderloin to go with it, but the filled squash alone would make a perfect light meal. As pretty as the filled squash halves were, it was easier to eat the filling when it's been scooped out of the rind. Function over form or something like that. I could see making the filling ahead of time and giving it a brief warming while the squash is baking, before filling and baking as per the recipe. This might make the recipe into a weeknight possibility. I used a Jonagold apple. I used two large shallots instead of the leeks, and added four small cloves of garlic, too. I used about 1/4 pound spinach for the greens. At first I thought this was too long since the squash was very soft and collapsed a bit. I was afraid it would overcook when I baked it again to warm the filling, but it didn’t. The texture was perfect when we ate it. I used a mixture of Jarlsberg and Manchego cheese. It did not end up looking like the cheese in the picture. I suspect that is finely grated Parmesan, from the looks of it. And it looks like it was added after the squash came out of the oven. I’m not sure the cheese added much and I might leave it off next time. Or mix it in. If I did use cheese, I think Parmesan would definitely be the best choice. The cheeses I used got a little leathery and dry in the oven.

It's always valuable for me to have some tasty fall recipes at my disposal as my garden is reaching it crescendo. This stuffed winter squash recipe utilizes a variety of fresh garden ingredients, which is a bonus. I used Delicata squash for this stuffed winter squash recipe. Because I have vegetarians in the house, I made some with vegetarian apple sausage and some with bacon. Both the bacon and the apple sausage received rave reviews. Jonathan apples and rainbow Swiss chard were available at our local farmer’s market and were terrific additions to the filling. Three leaves from the chard were more than sufficient for the greens. There was some white rice in pantry, so that made my grain choice easy. The preparation of the squash and the filling was simple but did take some time. I spent about 40 minutes chopping, slicing, and cooking. The bake time was 40 minutes for the squash to become fork tender and slightly caramelized, during which I prepped the filling. This filling would also work well for zucchini or bell peppers.

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