Roasted Winter Squash with Cilantro Chimichurri

Side DishVeganChimichurriDelicata Squash

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.

Photography Credit: 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.

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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

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.

Roasted Winter Squash with Cilantro Chimichurri Recipe

  • Prep time: 10 minutes
  • Cook time: 30 minutes
  • Yield: 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.


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


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

3 Roast the squash for 30 minutes or until easily pierced with a fork.

Roasted Winter Squash with Cilantro Chimichurri

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

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

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Garrett McCord

Garrett McCord is a professional writer and recipe developer whose work has appeared in many print and online publications such as Gourmet Live, Saveur, Huffington Post, Smithsonian, and NPR. Past clients also include numerous food companies, wineries, and distilleries. Garrett writes about cocktails on his website, Coupe de Grace.

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12 Comments / Reviews

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Did you make it? Rate it!

  1. Amanda

    Delicious! I’m glad I read the comments because I cut back on the garlic. Still plenty garlicky! The sauce is great. I had a lot left over for the amount of squash but I will put it to good use.



    Is the skin edible ? Thanks!

    Show Replies (1)
  3. Devon VB

    Omg, this is so good! Highly recommend!


  4. Annie Alba

    Hi, I haven’t made this yet, but what could I substitute cilantro with as it’s the one herb I cannot tolerate?

    Show Replies (1)
  5. Heather Holloway McCash

    Made this tonight and OMG it’s to die for. I will be making this chimichurri regularly and putting it on everything. I love acorn squash and never would have thought to combine the two. Thank you for this simple and amazing recipe.


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