Roasted Delicata Squash Harvest Kale Salad {Paleo, Whole30}

This harvest kale salad is packed to the max with goodies!  Perfectly roasted delicata squash, apples, pecans, and cranberries all tossed in a cider vinaigrette that’s naturally sweetened with dates.  Whole30, Paleo, vegan, and no refined sugar.

Is anyone else completely delicata squash obsessed lately?  It’s the one winter squash that I haven’t paid enough attention to all these years.  Really.

Roasted delicata squash is a savory, sweet, crispy treat that you’ll never want to be without.  Right now I’m loving it more than sweet potato fries, more than butternut squash, more than acorn squash.

I’ve been roasting it just to snack on, to be honest.  It’s just that good!  And in this epic Whole30 harvest kale salad, it’s definitely the hero.

What You’ll Need To Make this Roasted Delicata Squash Salad

This salad is loaded with flavor but doesn’t require anything crazy to throw it together.  For the salad, you’ll need:

Delicata Squash + oil and sea salt for roasting

Chopped Kale

Apples

Cinnamon

Pecans

Fruit-Sweetened Cranberries (this is the brand I love!)

For the dressing, you’ll need:

Medjool dates + water

Apple Cider Vinegar

Mustard

Cinnamon

Salt and pepper

Avocado oil, or olive oil

The dressing comes together FAST in a blender and it’s SOOO tasty.  One of those dressings I have to hold myself back from eating with a spoon 🙂

Tips for Roasting Delicata Squash

Delicata squash is amazing for a lot of reasons.  One of those reasons is that you don’t need to peel it!  Really, the peel is perfectly delicious to eat after roasting.  Here are a few of my tips for getting the perfect roasted delicata squash:

Slice it thin and evenly, for even roasting

Use parchment paper on the baking sheet to prevent sticking.  It also gets them crispier, in my opinion.

Spread them out so each slice has its own breathing room.  This will ensure they won’t steam.  You want them to roast up nice and crispy like French fries!  Using two baking sheets is essential for this recipe.

How to Make Salad Dressing with No Added Sugar

Of course, you could simply omit any sweeteners completely, but that wouldn’t be as tasty!  To sweeten up salad dressings while keeping things Whole30 compliant, I always use medjool dates.

The medjool dates are typically softer than other types, but I also soften them in hot water to make them really easy to blend up.  They add subtle sweetness and also a creamier texture to the dressing!

The dressing for this salad is a sweet apple cider vinaigrette.  I added a little mustard and cinnamon for an extra kick, and used avocado oil.  You can also use light flavored olive oil, but I don’t recommend extra virgin because it will take over the flavor of the dressing, giving it a bitter edge.

Lastly I wanted to mention massaging the kale.  Before I got into kale, I thought massaging it sounded odd and crazy to be honest.  As it turns out, it’s just an easy way to soften it up and make it perfect for salad!

Simply drizzle a little oil and sea salt on the kale and then just massage it with your hands.  You’ll feel it soften up, and depending on your preference you can massage it as long as you like to get the texture you prefer.

Okay, it’s time now guys!  Get ready to make this crazy delicious roasted delicata squash harvest kale salad – grab your squash and preheat the oven.  Magic is about to happen – let’s go!

Roasted Delicata Squash Harvest Kale Salad {Paleo, Whole30}

Roasted Delicata Squash Harvest Kale Salad {Paleo, Whole30}

This harvest kale salad is packed to the max with goodies! Perfectly roasted delicata squash, apples, pecans, and cranberries all tossed in a cider vinaigrette that’s naturally sweetened with dates. Whole30, Paleo, and no refined sugar.

Author: Michele Rosen

Prep Time: 15 minutes

Cook Time: 25 minutes

Course: Appetizer, Dinner or Side, Lunch

Cuisine: Paleo, Vegan, Whole30

Keyword: apples, delicata squash, salad, squash, winter squash

Servings: 8 servings

Print this Recipe

Did you make this recipe?

Leave a review

4.89 from 9 votes

Ingredients

Salad:

• 12 oz kale washed and chopped
• avocado oil and sea salt for massaging the kale
• 2 delicata squash
• 2 med/large apples cored and sliced into 1/2” slices
• 3/4 tsp ground cinnamon
• 1 cup pecans
• 2/3 cup Dried cranberries apple juice sweetened, for Whole30

Dressing:

• 2 medjool dates softened
• 3 Tbsp water
• 3 Tbsp apple cider vinegar
• 2 tsp mustard
• 1/2 tsp cinnamon
• 1/4 tsp sea salt fine grain, or to taste
• 1/8 tsp black pepper or to taste
• 1/3 cup avocado oil or light olive oil

Instructions

For the Squash:

1. Preheat your oven to 425° and line a large baking sheet with parchment paper. Wash the squash Cut ends off to create two flat edges. Cut in half lengthwise and scoop out seeds.
2. Cut into 1/4- to 1/2-inch slices, keeping the size of the slices consistent. Rub, toss, or spray with olive oil so both sides of each slice are coated with oil. Sprinkle with salt and pepper and spread onto a parchment paper lined baking sheet in a single layer.
3. Place in preheated oven and roast for 25-30 minutes, flipping after 15 minutes or so. Once they appear golden brown and crisp, remove from the oven.

Apples and Pecans:

1. Spread out the apple slices on a large parchment lined baking sheet and sprinkle with the cinnamon. Roast in the preheated oven (below or above the squash for 7-9 minutes or until tender.
2. After 5 minutes, sprinkle the pecans over the apples and continue to roast 2-4 minutes, watching the pecans to avoid burning.

For the Dressing:

1. Place all dressing ingredients in a small high speed blender (I used a NutriBulleand blend until smooth. Set aside until ready to serve.

Arrange the Salad:

1. Place the chopped kale in a large bowl and drizzle with 1-2 Tbsp oil and sprinkle with sea salt. Massage the kale for several minutes until you reach desired texture.
2. Layer the kale with the roasted delicata squash, apples, pecans, and the dried cranberries. Toss with the dressing before serving. Keep leftovers covered in the refrigerator for up to 4 days. Enjoy!

Nutrition

Calories: 275kcal

Carbohydrates: 28g

Protein: 4g

Fat: 19g

Saturated Fat: 2g

Sodium: 109mg

Potassium: 698mg

Fiber: 4g

Sugar: 14g

Vitamin A: 5812IU

Vitamin C: 65mg

Calcium: 112mg

Iron: 2mg

Did you make this recipe?

Tag @PaleoRunningMomma on Instagram and hashtag it #PaleoRunningMomma

Shop Products and Ingredients:

Want More Paleo + Whole30 Salad Recipes?  Try One of These!

Kale Chicken Caesar Salad

Brussels Sprouts Salad with Bacon and Apple Vinaigrette

Kale Salad with Caramelized Onions, Chicken, and Hot Bacon Dressing

Rainbow Power Veggie Salad 

Roasted Butternut Squash Salad with “Buttermilk” Dressing

Note: This post contains Amazon affiliate links. This means that if you click on a link and make a purchase, I will receive a small commission at no cost to you. Thank you for supporting Paleo Running Momma!