Roasted Winter Squash with Cilantro Chimichurri

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.

  • Prep time: 10 minutes
  • Cook time: 30 minutes
  • Yield: 6 to 8 servings


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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  • 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?

  • 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.


  • Mary

    I made this recipe. Loved the squash. I ordered the urfa biber and used it in the sauce. I doubled the recipe because I had a lot of herbs. I liked the herb/ spice mix, but thought the taste of garlic was overpowering. I am going to try again but use roasted garlic this time.

  • Sandy S.

    Garrett, I have hit the mother-lode of winter squash in that my neighbor has had a bumper crop and is dropping them by my doorstep like the daily mail. Will be trying your recipes on a butternut tonight! As to becoming an adult…reserving turning up the thermostat until you could afford to pay for it, sounds pretty adult to me. Perhaps this is how some bakers/chefs are hatched!?!

    • Sandy S.

      Turned out great! I peeled the butternut and used regular chili flakes in the chimichurri, which is killer! Will look for the urfa biber. It sounds pretty interesting.

  • Marta Rivera

    Ah-mazing! This recipe was a hit for my entire family. My carnivorous husband ate three helpings, and my twelve year old twins asked for seconds.