Kale Salad with Caramelized Squash + Maple Orange Dressing

Your seasonal fall menus need a fresh counterpoint, and this Fall Salad with Caramelized Squash + Maple Orange Dressing is IT. To make it, roast cubed up butternut squash and while it roasts, prepare the rest of the salad. I can’t get enough of the dressing in this recipe, which essentially marinates the kale so every bite is super flavorful. Check out the “Let’s Riff” section at the bottom of the recipe because spoiler alert: this salad is endlessly riffable. Swap in your favorite seasonal veg in place of the butternut squash, get creative with the toppings, and make it your own.

Kale Salad with Caramelized Squash + Maple Orange Dressing

Your seasonal fall menus need a fresh counterpoint, and this Kale Salad with Caramelized Squash + Maple Orange Dressing is IT. Serves 6.

Prep:
15
min
cook:
45
min
total:
60
min
Ingredients

For the salad:

  • 1 lb butternut squash, cubed (or about 3 cups any seasonal root veg, i.e. delicata squash, beets, sweet potatoes, or carrots)
  • 2 tablespoons extra virgin olive oil
  • 2 bunches dino kale, also known as Tuscan kale or lacinato kale, stems removed 
  • 1/2 cup pepitas
  • 1/2 cup pomegranate arils, and/or dried cranberries, or thinly sliced apple, pear, or persimmon
  • Handful or two crumbled goat cheese, feta cheese, or blue cheese
  • Optional: few slices crispy bacon, crumbled 

For the vinaigrette:

  • 1 clove grated garlic or 1 finely chopped shallot
  • 2 tablespoons apple cider vinegar
  • zest and juice of 1 orange
  • 1 tablespoon maple syrup
  • 1 tablespoon dijon mustard 
  • 1/3 cup extra virgin olive oil
  • Kosher salt and cracked black pepper to taste

Instructions

Roast the squash

  1. Preheat oven to 425*F.
  2. Toss butternut squash with Sizzle Extra Virgin Olive Oil, and few generous pinches of kosher salt. Arrange on baking sheet and roast for about 35-40 minutes, or until squash is caramelized on the outside and fork-tender, being sure to toss squash about halfway through.

Make the vinaigrette + prep rest of salad

  1. While the squash is roasting, make the vinaigrette. To large bowl or jar, add garlic, apple cider vinegar, orange zest and juice, maple syrup, dijon mustard, and few generous pinches kosher salt. Let sit for about 5 minutes to macerate the garlic. Whisk in olive oil until combined.
  2. Roughly chop the kale and toss in vinaigrette and really massage it with your hands for a minute. This helps take off that super intense earthy bite, and the kale will essentially marinate in the dressing as the rest of the dish comes together. 
  3. After you prep the kale, toast pepitas in skillet over medium heat for about 4-5 minutes, stirring frequently, until they are lightly browned and crunchy. Set aside.

Finish + serve

  1. When the butternut squash is done roasting let cool for several minutes.
  2. In large serving bowl, toss dressed kale with half of the butternut squash, half of the pepitas, half of crumbled cheese, and half of the pomegranates to evenly coat in dressing.
  3. Top salad with remaining ingredients and serve!  (Pro tip: tossing the greens with half of the toppings and finishing with the remaining toppings prevents all of the fixins from falling to the bottom of the bowl, you’re welcome).

Let's riff
  • The Butternut Squash: Any kind of fall or winter squash or hardy veg works, i.e. delicata or honeynut squash, carrots, beets, etc.
  • The Kale: Use curly kale if needed.
  • The Orange: Sub in lemon.
  • The Maple Syrup: Sub in honey or date syrup, or omit all together.
  • The Apple Cider Vinegar: Sub in any vinegar as needed, I love champagne or red wine vinegar here.
  • The Toppings: I like the balance of a toasted nut or seed, a fresh fruit or two, and a crumbly cheese. My go-to's are toasted pepitas, pomegranate arils and sliced apples, and crumbled goat or blue cheese. Sub in pecans or walnuts in place of pepitas, pears, persimmons, or citrus segments as the fruit, or feta or ricotta salata for the cheese. Crispy crumbled bacon is also a *very* delicious topping.

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Jenna Symon
July 15, 2024
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March 23, 2024
Gini
March 20, 2024
Loved the soup. Croutons too much trouble. Fast in a cup!
Ray Beall
March 16, 2024
Richard
February 22, 2024
send me fruits to add with another fruit to cure disease
Deneen Medland
April 17, 2023
Kelle Trouton
April 17, 2023
Caroline
January 23, 2023
I made this same amazing salad with the following additions: I used a bed of chopped romaine hearts, and squeezed the juice of all the trimmed cara cara oranges, plus 1/2 lemon, added a drizzled of Tupelo honey on top. The herbs: chopped fennel fronds and mint. Everyone went crazy for it!
Marcus
YUM! Definitely going to pair this with a nice and funky natty white next time!
Caroline
January 23, 2023
I made this same amazing salad with the following additions: I used a bed of chopped romaine hearts, and squeezed the juice of all the trimmed cara cara oranges, plus 1/2 lemon, added a drizzled of Tupelo honey on top. The herbs: chopped fennel fronds and mint. Everyone went crazy for it!