Roasted Winter Squash with Cilantro Chimichurri

Roasted Winter Squash with Cilantro Chimichurri! Use a mix of squashes, like acorn squash and delicata squash. The cilantro chimichurri makes this simple dish into a showstopper.

Garrett McCord
Garrett has been writing about food and sharing recipes for 15 years. He is the author of Melt: The Art of Macaroni and Cheese.
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Garrett McCord
Published October 31, 2017
Garrett McCord
Roasted Winter Squash with Cilantro Chimichurri
Elise Bauer

We’ve all had those shocking epiphanies where suddenly you realize that somehow, someway, you’ve become an adult.

Maybe it was when you found yourself agreeing with Ariel’s dad in The Little Mermaid. (“Young lady, you don’t love that boy. You don’t even know him!”) Or perhaps it was when you realized you actually wanted socks for your birthday because that meant you wouldn't have to spend your own money on them.

For me, it was when I first used the thermostat after getting my first real job after college. Before, I was simply wearing a lot of sweaters and ensuring that whatever I made for dinner required turning on the oven so it would also warm the tiny hovel my landlord passed off as an apartment.

Suddenly, I was an adult with a heating bill.

Roasted Winter Squash with Cilantro Chimichurri
Elise Bauer

Still, some of those heat-the-apartment recipes that I cobbled together in my pre-adulting days were nothing less than epic. I still make them today!

Take this recipe for roasted winter squash with cilantro chimichurri: super cheap ingredients and crazy easy to make. Yet, the result is always breathtaking. Bright, herbal, acidic, and sweet. It's the perfect cold weather dish on a budget – that also requires turning on the oven.

Even better? When you serve it to your friends, you’ll convince everyone you're a real adult with excellent taste.

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Roasted Winter Squash with Cilantro Chimichurri

Prep Time 10 mins
Cook Time 30 mins
Total Time 40 mins
Servings 6 to 8 servings

I typically use acorn or delicata squash for this recipe since they don’t have to be peeled and are easily prepped, though feel free to use any other hearty winter squash like butternut, pumpkin, or kuri. The chimichurri sauce is also great on roasted potatoes, carrots, and sweet potatoes.

Urfa biber is a dark maroon chili flake common in Turkish cuisine. A super adulty spice. The chilies are sun-cured during the day and sweated at night before being ground with a touch of salt. The result is a smoky-salty-sweet-savory chili flake whose complex flavor is reminiscent of chocolate, raisins, and inky red wine. The heat is mild, but builds the more you eat, yet never overwhelms. It’s one of those rare ingredients that really can go on nearly everything. I actually keep it in a small container on the kitchen table for this reason and recommend you do so as well.

You can find urfa biber pretty easily online at stores like Spice Jungle or Olive Nation. However, if you don’t have urfa biber chili flakes, then feel free to use regular chili flakes. I have done this plenty of times and the recipe is equally awesome.

Ingredients

  • For the squash:
  • 3 pounds acorn or delicata squash
  • 1 tablespoon olive oil
  • 1/4 teaspoon salt
  • Ground black pepper
  • For the cilantro chimichurri:
  • 1/2 cup olive oil
  • 1/2 cup finely chopped cilantro
  • 1/2 cup finely chopped parsley
  • 1 tablespoon finely chopped oregano leaves
  • 1 1/2 teaspoons urfa biber, or regular chili flakes
  • 1/4 teaspoon salt
  • 4 garlic cloves, minced
  • 1/4 cup red wine vinegar

Method

  1. Preheat the oven to 375F:

    Line a baking sheet with aluminum foil, a silicon baking mat, or parchment paper.

  2. Prepare the squash:

    Cut the squash in half lengthwise. Scoop out and discard the strings and seeds (save and roast the seeds, if you like). Cut the squash into 1-inch slices.

    Toss the squash with a 1 tablespoon of olive oil, 1/4 teaspoon or so of salt, and ground black pepper. Place on the prepared baking sheet.

    Roasted Winter Squash with Cilantro Chimichurri
    Elise Bauer
  3. Roast the squash for 30 minutes:

    or until easily pierced with a fork.

    Roasted Winter Squash with Cilantro Chimichurri
    Elise Bauer
  4. While the squash is cooking prepare the chimichurri:

    In a medium bowl, stir together the olive oil, cilantro, parsley, oregano leaves, chili flakes, garlic, red wine vinegar and 1/4 teaspoon salt. Taste and add more salt if needed.

    Roasted Winter Squash with Cilantro Chimichurri
    Elise Bauer
  5. Serve:

    Transfer the roasted squash to a serving platter or individual plates, top with a generous amount of chimichurri, and enjoy.