Dressings and Marinades Sides and Snacks

Roasted Delicata Squash with Chimichurri

I am a sweet potato fiend, so have been trying to branch out into squashes to diversify my winter sides. Little did I know, delicata squash, the first squash I tried branching out to, was known as “sweet potato squash.” Par for the course, I guess.

I came across this recipe waiting for a train, of all places, where Whole Foods had a massive poster advertising their holiday recipes. This is the only one I’ve tried, but it’s for sure a keeper. We made it as part of our Christmas dinner and it was a big hit that night, as well as leftover the next few days.

For entertaining, I highly recommend making the whole recipe, including the chimichurri. For an everyday meal, the chimichurri is great, but you’d be fine simply roasting the squash without a dipping sauce.

Best For– Sweet potato and squash fans looking for a unique recipe for a holiday dinner or weekday winter meal.

Musical Pairing– “Piece of Me” by Lady Wray


For the squash-

  • 3 Delicata squash (try to pick evenly sized ones)
  • 1 tablespoon extra-virgin olive oil
  • Salt and pepper to taste

For the chimichurri-

  • 2 cups packed fresh parsley
  • ¼ cup loosely packed fresh oregano leaves, stripped from stems
  • 2 tablespoons chopped fresh sage leaves
  • 2 cloves garlic, peeled and smashed
  • 1 teaspoon smoked paprika
  • ½ teaspoon ground fennel
  • ½ teaspoon crushed red chile flakes
  • 1 teaspoon kosher salt
  • ¼ cup apple cider vinegar
  • ½ cup extra-virgin olive oil


  1. Preheat oven to 400 degrees
  2. While preheating, wash off the squash. Cut off each end. Then cut the squash in half. Using an ice cream scooper, take out the insides of the squash. Then cut in 1/2 slices. Put slices in bowl with olive oil, salt, and pepper
  3. On a lined baking sheet, place squash sliced. Put in oven for 40 minutes, flipping over halfway through
  4. While squash is cooking, make your chimichurri. Combine all ingredients in food processor and blend until smooth. Refrigerate until ready to serve.
  5. Either drizzle the chimichurri lightly over the squash or serve on the side. Keep any extra for bowls, steak, other roasted veggies, etc. in an airtight container in the fridge. Enjoy!

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