Southborough, MA | A Trustees Property

Kale & Squash Salad

You will know this is Jeff, not Des speaking because of what I am about to say: I made my first raw kale salad last weekend. While I have been cooking up a kale storm all season, I only just now worked up the courage to pour on the olive oil and massage those leaves. I was surprised that kneading kale like dough produced the desired result. It turned out great and was a big hit.

While I roasted kabocha squash (1/2″ cubes at 400 degrees for 35 mins.), this recipe uses delicata. I am sure any of our winter squashes would work and we have all varieties for sale. If you’re looking to avoid a trip to the grocery store, make your way into the farm stand for the garlic, syrup, olive oil, and apples if you need them. I also bet that goat cheese and dried cranberries would make a great addition.

If I can do it, so can you! Enjoy the flavors of fall.


  • 1 medium delicata squash, very thinly sliced into 1/2moons and seeds removed 
  • 2 cups butternut squash cubes
  • 1 tablespoon olive oil
  • salt/pepper 
  • 1/2 cup walnut halves 
  • 2 tablespoons pure maple syrup
  • 1/8 teaspoon ground cinnamon
  • 1/8 teaspoon ground nutmeg
  • 2 large bunches Tuscan kale, ribs removed and very thinly sliced into ribbons 
  • 2 sweet, crisp apples (like Honeycrisp, Pink Lady, Gala), very thinly sliced 

Cinnamon-Maple Dressing: 

  • 2 tablespoons apple cider vinegar
  • 1 tablespoon pure maple syrup 
  • 1 teaspoon dijon mustard
  • 1 medium garlic clove, minced 
  • 1/4 teaspoon ground cinnamon
  • 1/2 teaspoon salt
  • 1/4 teaspoon ground pepper 
  • 1/3 cup extra-virgin olive oil 


  1. Preheat oven to 400 degrees F. Toss squashes with 1 tablespoon oil oil and pinch salt and pepper. Place on a single layer on a baking sheet and roast until tender, about 25 minutes, flipping once during cooking. 
  2. Heat the walnuts in a nonstick skillet over low heat, stirring often until just toasted. Stir in the maple syrup, cinnamon and nutmeg. Let the maple syrup bubble up around the walnuts, then transfer to a piece of parchment paper to let cool completely.  
  3. While the squash is cooking, cut the kale. Remove the tough center rib and stack the leaves. Tightly roll and slice from the end, creating thin strips. Place in a large bowl and set aside.
  4. Right before serving, massage 1-2 tablespoons of the dressing into the kale. Add the squash and candied walnuts. Right before serving, slice the apples and add them along with dressing. Serve immediately.

Thanks to