Roasted Squash Salad with Parmesan-Peppercorn Dressing

Of all the winter squash varieties, delicata, with its oblong shape and beautiful green striations, is the easiest to work with. Nicknamed the “sweet potato squash,” it has a sweet, velvety flesh that caramelizes beautifully in the oven.

It’s so low maintenance that it doesn’t even require peeling.

I love tossing the squash in a chili-maple mixture for a sweet-spicy contrast. The texture and sweetness pari beautifully with fibrous kale, however you could also use arugula in this salad.

I especially love the Parmesan-Peppercorn dressing in this recipe. It’s rich and nutty with a good dose of umami from the Parmesan.

How to Make Roasted Squash Salad

This salad pairs well with an array of entrees or protein.

It feels special enough for the holidays, yet is also weeknight-friendly.

You can serve it as an entree with the addition of your protein of choice (shredded chicken, salmon, or chickpeas). Or, serve it alongside a pot roast, meatloaf, or your favorite holiday main.A white serving bowl filled with roasted squash and kale salad and drizzled with creamy dressing

The Ingredients

  • Delicata Squash: Delicata squash is much smaller than most winter squash varieties. It also tends to have a richer flavor and creamier consistency. The best time to cook it and enjoy it is early fall – perfect timing for this salad!
  • Kale: The beauty of kale is that it can be dressed ahead of time and still stay crisp. This is ideal if you’re preparing the salad in advance. 
  • Red Onion: Red onion roasts alongside the delicata squash for an aromatic addition to the salad.
  • Spices: A mix of chili powder and garlic powder season the squash. You can also toss in some paprika and/or cumin.
  • Maple Syrup: The sweetness helps balances the chili powder in the squash mixture.
  • Walnuts: A fantastic source of omega-3 fats, walnuts add richness and crunch.
  • Panko: Toasted panko takes the place of croutons, adding crunch and texture to each bite.
  • Parmesan: Freshly grated Parmigiano-Reggiano has a sharp, complex flavor that elevates the dressing.
  • Pepper: Freshly cracked peppercorns (black or mixed) add a hint of spice to the dressing.
  • Mayonnaise: I prefer avocado oil mayo, such as Sir Kensington’s brand. Alternatively, use full-fat Greek yogurt.
  • Lemon: For a punch of brightness and acidity. 

The Directions

Step 1: Season Squash and Red Onion

Slice delicata squash in half lengthwise and scoop out seeds. Cut the halves again lengthwise to create four segments.

Slice each segment into ½-inch thick pieces.

Combine squash, onion, olive oil, maple syrup, thyme, spices, and salt in a large bowl; toss well to coat.Sliced delicata squash and red onion in a large bowl being tossed in oil, spices, and herbs

Step 2: Roast Vegetables

Arrange veggies on a baking sheet and roast for 35 minutes, tossing halfway through.Veggies being roasted on a rimmed baking sheet

Step 3: Prepare Parmesan-Peppercorn Dressing

In a bowl, combine mayonnaise, lemon juice, Dijon, black pepper, and salt. Gradually stream in olive oil, while whisking constantly. Stir in Parmesan and set aside.Parmesan Peppercorn dressing being whisked in an orange bowl

Step 4: Toast Walnut-Parmesan Breadcrumbs

Spread walnuts, Parmesan, and breadcrumbs out on a baking sheet, and toss with olive oil. 

During the final 10 minutes of the veggie roasting, place pan in the oven. Bake for 7 to 10 minutes, watching closely to avoid burning, and shaking the pan every few minutes, until nicely golden.Walnuts, parmesan, and panko being toasted on a baking sheet

Step 5: Assemble Salad

Place kale in a large bowl along with half of the dressing. Massage the dressing into kale leaves for about 30 seconds until the greens are soft.

Top with squash and red onion, along with half of the breadcrumb mixture; toss to combine. Spoon remaining dressing overtop, and garnish with remaining breadcrumbs.Kale, roasted veggies, and dressing being assembled in a wooden bowlWalnut-parmesan breadcrumbs being scattered over assembled salad

Expert Tips for Cooking Delicata Squash

One of my favorite things about delicata squash is how easy it is to prepare. Plus, this roasting method only takes about 35 minutes.

  • Cut the Squash: Because you can eat the skin, there’s no need to peel the squash before you chop it. Start by slicing it in half lengthwise. Then, use a spoon to scrape out the seeds and stringy flesh.
  • Season the Squash: This is where the versatility lies. Delicata squash pairs well with just about any spice combo. I love using a mix of sweet and spicy flavor agents, such as maple syrup, chili powder, cumin, and smoked paprika.
  • Roast the Delicata Squash: Once the squash is oiled and seasoned, spread it on a rimmed baking sheet, avoiding any overlap. Roast the squash at 425ºF for 35 minutes, turning once halfway through.

If you give this recipe a try, be sure to snap a pic and tag #dishingouthealth on Instagram so I can see your creations. Also, follow along on Facebook and Pinterest for the latest recipe updates!

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