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Roasted Butternut Squash, Tomato, and Arugula Salad with Cranberry-Orange Vinaigrette

Peppery arugula is tossed with roasted butternut squash and tomatoes, toasted pine nuts, and juicy pomegranate seeds. The combination is made all the more festive with a generous drizzle of cranberry-orange vinaigrette. This salad is packed with vitamin A and vitamin C, making it an ideal immunity-boosting and festive fall meal.
Prep Time20 mins
Cook Time25 mins
Total Time45 mins
Course: Salad
Cuisine: Gluten-Free, Grain-Free, plant-based, Vegan
Author: Ashley


Roasted Butternut Squash and Tomatoes

  • pound One small 1- butternut squash, peeled
  • 2 cups grape or cherry tomatoes, halved or quartered (or a mix of both)
  • 1 ½ tablespoons extra-virgin olive oil, divided
  • 2 teaspoons smoked paprika, divided
  • 1 teaspoon ground cinnamon
  • Sea salt, to taste
  • Freshly ground black pepper

Cranberry-Orange Vinaigrette*

  • cup thawed frozen cranberries, juices drained
  • 1 tablespoon fresh orange zest (zest of about 1 medium orange)
  • ¼ cup freshly squeezed orange juice
  • ¼ cup cold-pressed olive oil
  • 3 tablespoons apple cider vinegar
  • 1 tablespoon pure maple syrup
  • ¼ teaspoon sea salt
  • Freshly ground black pepper, to taste


  • 5 ounces baby arugula
  • ¾ cup pomegranate seeds (the seeds from about 1 medium pomegranate)
  • ¼ cup toasted pinenuts


For the Roasted Butternut and Tomatoes

  • Preheat the oven to 400F. Line two large rimmed baking trays with parchment paper.
  • Use a sharp knife to carefully slice the peeled squash in half. Scoop out the seeds and discard. Cut the squash into small, ½-inch cubes and transfer to one of the lined baking trays. Drizzle with 1 tablespoon of the olive oil and sprinkle with 1 teaspoon of the smoked paprika, and the cinnamon. Season with sea salt and black pepper. Toss to coat.
  • Add the halved cherry tomatoes to the other lined pan, drizzle with the remaining ½ tablespoon olive oil, and sprinkle with the remaining 1 teaspoon smoked paprika. Season with sea salt and black pepper. Toss to coat and spread out into an even layer across the pan.
  • Transfer both pans to the oven. Roast the tomatoes for 15 to 18 minutes, or until tender, blistered, and just beginning to turn golden-brown at the edges. Roast the butternut squash for 20 to 25 minutes, or until fork tender and just beginning to caramelize, flipping at the 15-minute mark.
  • Remove both pans from the oven and let cool slightly.

For the Cranberry-Orange Vinaigrette*

  • Meanwhile, add all the vinaigrette ingredients to a food process and process for 20 seconds, or emulsified. The cranberries should be very finely chopped.

To Assemble

  • Divide the arugula between bowls or plates. Top with the pomegranate seeds, pinenuts, and roasted butternut squash and tomatoes. Drizzle each salad with as much of the vinaigrette as desired and serve immediately.


*Alternatively, you can make this Balsamic Vinaigrette (with or without the thyme leaves) for a tangier, more savory variation.