Butternut Squash, Cranberry & Kale Salad With Creamy Avocado-Pear Dressing

Oh, butternut squash, how I love and loathe thee. You make wonderful soups, roast to a delicious mix between sweet and savory, are packed with vitamin A and add really great color to food photos. However, you are a complete pain in the ass to cut. Every time I post or say that, someone tells me their tried-and-true way to make cutting squash easier but in the end I still end up with stringy goop between my fingers and under my nails. But I still keep coming back.

As much as I love the abundance of spring and summer produce, the fall harvest has my heart. From pumpkins to pears to squash to chestnuts, I love everything about this season. In general I’m a pretty boring salad maker and I don’t post many salad recipes here for that reason. I’m greens + dried fruit + dressing kind of person and that’s not an interesting recipe post (believe me, I’ve read them). However, throw together a mix of seasonal ingredients, bold flavor combinations, and an interesting dressing and my mouth starts to water.

Let me wax poetic about homemade salad dressings for a minute…

I make most of my dressings at home after a formative salad dressing experience (only someone obsessed with food would say that) during my undergrad hospitality class. For an entire semester I was required to spend one morning a week “learning” in the kitchen of our university restaurant…on top of working 4-5 nights a week at a restaurant because I had big-girl bills to pay. Let’s just say I was a bit bitter to spend 4-5 hours working for free for a class I was paying for and then leaving to work all night at my restaurant job to pay for said class, but that’s a story for another day. But one good thing came out of that time period: I learned to make my own salad dressings.

The chef of the university restaurant was like most chefs I’ve worked with: scary and feared my all. He was an Irish man who never smiled and toed the line between being stern and harassing the students. One day he put me in the salad station and said, “Make a shallot white wine dressing for 100 people.” No explanation, no list of ingredients, nothing. So I started throwing whatever sounded good into the food processor and hoped for the best. When we finally came over to check on my he dipped his finger (!) in the dressing, looked at me and said, “It’ll do.”

It was the nicest thing he ever said to me and I’ve been making my own dressings ever since.


Butternut Squash, Cranberry & Kale Salad With Creamy Avocado-Pear Dressing

A heart, autumn salad of kale, cranberries and butternut squash with a vegan creamy avocado pear dressing.

  • Author: Kristina Todini
  • Prep Time: 10 mins
  • Cook Time: 30 mins
  • Total Time: 40 minutes
  • Yield: 2 dinner size salads
  • Category: Salads


For Salad

  • 1 medium butternut squash, cut into 1 inch cubes
  • 1 shallot, sliced
  • 2 tsp olive oil
  • salt and pepper (use your own judgement)
  • 4 cups kale, chopped into bite-size pieces
  • 1/4 cup dried cranberries

For Creamy Pear Dressing

  • 1/2 avocado
  • 1/2 pear, cut into small pieces
  • 1/8 cup white wine vinegar
  • 1-2 tbsp honey
  • pinch salt
  • ground black pepper (again, use your judgement)
  • 1/4-1/3 cup olive oil


  1. Heat oven to 400 degrees.
  2. Toss squash and shallots with olive oil, salt, and pepper and roast until golden brown. My trick for perfectly browned squash: Leave in oven for 15-20 minutes untouched, or until sizes are browned. Then flip every 5 minutes or so until golden brown, but not burnt.
  3. For dressing: add avocado and pear to food processor or hand mixer and chop until smooth(ish). Add white wine vinegar, honey, salt, and pepper and mix until combined. Then slowly add olive oil until desired consistency and salt and pepper to desired taste. I wanted my dressing to be a bit thicker to stick to the kale leaves, but you do you.
  4. When butternut squash is done, combine it with the cranberries and kale in a bowl and top with dressing. I used my hands to rub dressing into the kale to coat throughout.
  5. Enjoy! It holds up well refrigerated and tasted great the next day for lunch leftovers.