A Grateful Meal

Roasted Squash Salad

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Roasted acorn squash on top of massaged kale salad with pecans, shaved Parmesan, and dried cranberries with serving utensils
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I am all about that Thanksgiving prep lately. Have you been able to tell? This autumn roasted squash salad is no different. You can make this salad ahead of time and let it hang out in the fridge until mealtime, which is perfect considering all the day of Thanksgiving cooking that often needs to happen.

I love the flavor combination of this recipe. The greens are dressed in a tart and sweet dressing topped with dried cranberries, toasty nuts, and salty, shaved parmesan cheese. It’s all rounded out with the caramelized and buttery quality of the roasted acorn squash. It’s so good that my husband requested that I make it for his company Thanksgiving potluck. This is perfect because it helps offer a different vegetable option for the party, and keeps well when made in advance. 

Close up of roasted acorn squash on top of massaged kale salad with pecans, shaved Parmesan, and dried cranberries in a bowl
Overview of roasted acorn squash on top of massaged kale salad with pecans, shaved Parmesan, and dried cranberries in a bowl
This post contains links that pay me a small commission at no extra cost to you.

Honestly, this roasted squash salad is perfect for everyday meal prep too. I love making hardy green salads in the winter. My favorite go-to green for fall/winter salad-making is kale. I hear a lot of people don’t like kale in salads because it’s so tough and fibrous. Well, sorry to break this to you, but you’re probably doing it wrong. The best kale salads are allowed to marinate in an acidic dressing or vinegar for long periods, or you can speed the process up by massaging the dressing or vinegar into the greens. The acid works the way that heat does in cooking greens; it allows for the fibers to break down, making the greens soft and tender. Even if you massage the greens, you can still make the salad ahead of time without it being too wilted. 

I’ll be making this salad for months to come for sure, and once you try it, I’m sure you will too. 

P.S. If you’re all about that Thanksgiving prep, too, make sure that you join my email list. I’ll be sharing all things holiday food and lifestyle from now until New Year’s. 

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Roasted Squash Salad

Overview of roasted acorn squash on top of massaged kale salad with pecans, shaved Parmesan, and dried cranberries in a bowl
  • Cook Time: 30 minutes
  • Total Time: 30 minutes
  • Yield: 0 servings 1x
Scale

Ingredients

  • 1 medium acorn squash, seeded, sliced (skin is edible!)
  • 1 tbsp. fresh sage, minced
  • 1/4 cup + 1 tbsp. olive oil, divided
  • salt and pepper, to taste
  • 1 tbsp. dark fruit jam (like cherry or blackberry)
  • 2 tbsp. balsamic vinegar
  • 6–8 cups kale, chopped
  • 2–3 oz. (or more to taste) parmesan cheese, shaved
  • 1/4 cup pecans, toasted
  • 1/4 cup dried cranberries

Instructions

  1. Preheat oven to 410 degrees F. Toss sliced acorn squash, sage, 1 tbsp. olive oil, and salt and pepper on a sheet pan. Roast squash for 20 minutes. Flip squash, rotate the pan for even cooking, then roast for another 10 min.
  2. Meanwhile, make dressing by whisking together jam, vinegar, 1/4 cup olive oil, and salt/pepper to taste. (Or put dressing ingredients in a mason jar, seal, and shake until incorporated.)
  3. Massage kale with dressing until slightly wilted about 2-3 min. Once squash is done roasting, top kale with squash, cheese, pecans, and dried cranberries.