Roasted Squash and Kale Salad

Are you into squash? I don’t eat enough of it but it’s delicious when made right. I kind of default to putting cinnamon/brown sugar/cayenne on it most of the time but there’s just something about the mix of spice and sweetness.

Kale can be a tough customer, and I think a lot of people don’t realize you have to “massage” kale in order to eat it raw. It’s a strong, fibrous plant, and massaging it breaks down its cell walls somewhat making it nicer to eat and easier to digest!

There are a million iterations of this salad, commonly served with pomegranate seeds instead of dried cranberry but I personally don’t like chewing on them. Swap the kale for spinach, use acorn, delicata or butternut squash.

What you need:
Serves 4-6

  • 1 large acorn squash, peeled and sliced 1/2″ (about 3 cups)
  • 2 tbsp olive oil, divided
  • 1 tbsp brown sugar
  • 1 tsp cinnamon
  • 1/4 tsp red chili flakes
  • 1/2 tsp salt
  • 1/4 tsp pepper
  • 5 cups kale, washed
  • 1-2 tbsp lemon juice
  • pinch salt
  • 1/4 cup feta, crumbled
  • 3 tbsp dried cranberries
  • 3 tbsp toasted pumpkin seeds


  • 2 tbsp honey
  • 2 tbsp grainy mustard
  • 3 tbsp apple cider vinegar
  • 1/4 cup olive oil
  • 1/2 tsp salt
  • 1/2 tsp pepper

Preheat oven to 400F. Prepared a large parchment lined baking sheet.

  1. In a large bowl combine peeled sliced squash, 1 tbsp of olive oil, brown sugar, cinnamon, chili flakes, salt and pepper. Toss to coat and place in an even layer onto baking sheet. Bake for about 20-25 minutes or until squash has browned lightly and piercing with a fork provides no resistance. Let cool slightly.
  2. We gotta massage that kale. In another bowl place kale, and tear into 1″ chunks, removing any of the stems. Add lemon juice, remaining 1 tbsp of olive oil and pinch of salt. Gently massage the leaves by rubbing them between your fingers and distribute the oil/juice for a few minutes. (I’ve included a video below if this doesn’t make sense!)
  3. In a bowl, combine all dressing ingredients except for oil. Whisk to combine, then carefully stream the oil in while whisking continually to emulsify. Set aside.
  4. On a large platter lay out kale, place pieces of squash on top and throughout. Top with feta, dried cranberries and pumpkin seeds.

Serve with dressing and Enjoy!


How to massage kale:


6 thoughts on “Roasted Squash and Kale Salad

  1. That’s a beautiful salad. When I cook any kind of squash like pumpkin, butternut, or acorn, I use olive oil and garlic pepper. I noticed you used brown sugar, and thankfully, only 1 tablespoon of it! I can eat squash with a spoon when it’s just baked with garlic pepper, or just salt, cause it’s so good and already sweet to me. Same with sweet potatoes. I love what you did overall, don’t get me wrong.Love the cranberries and pumpkin seeds. The salad is wonderful At least you didn’t add marshmallows!!!

    Liked by 1 person

    1. That’s the joy of cooking because we can just make it to our own tastes! I’m definitely more of a savoury person myself, so this is probably as sweet as I’d make anything, especially as a special occasion kinda dish! And haha! The marshmallow and potato thing I’ve never understood but maybe that’s because I’m canadian <_< 😛


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