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Best Roasted Delicata Squash & Cranberry Fall Salad

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This roasted delicata squash and cranberry fall harvest salad is simple enough for a weeknight, but special enough to serve at a holiday table. The combination of sweet, caramelized squash, tart cranberries, peppery arugula, and creamy tahini dressing is one of those flavor pairings that just works.

Ingredients

Scale
  • 2 medium delicata squash (about 2 pounds total)
  • 3 tablespoons olive oil, divided
  • 2 tablespoons plus 1 teaspoon maple syrup, divided
  • 1/2 teaspoon ground cinnamon
  • 1/4 teaspoon smoked paprika
  • Kosher salt and black pepper to taste
  • 5 ounces baby arugula (about 5 cups)
  • 1/2 cup dried cranberries
  • 1 medium apple (such as Honeycrisp or Fuji), cut into thin matchsticks or small cubes
  • 1/3 cup toasted pepitas
  • 1/3 cup crumbled feta or goat cheese (optional)
  • For the Maple-Tahini Dressing:
  • 3 tablespoons tahini
  • 2 tablespoons maple syrup
  • 2 tablespoons apple cider vinegar
  • 2–3 tablespoons warm water
  • 1/4 teaspoon salt

Instructions

  1. Preheat your oven to 400°F (200°C) with a rack in the middle position. Line a large baking sheet with parchment paper.
  2. Wash the delicata squash well, trim off the ends, slice in half lengthwise, and scoop out the seeds. Cut each half into half-moons about 1/2-inch thick.
  3. Place the squash slices on the prepared baking sheet. Drizzle with 2 tablespoons olive oil, 1 teaspoon maple syrup, cinnamon, smoked paprika, and a generous pinch of salt and black pepper. Toss to coat. Spread in a single layer and roast for 20-25 minutes, flipping halfway through, until tender and golden brown. Let cool on the pan for 5 minutes.
  4. While the squash roasts, toast the pepitas in a dry skillet over medium heat for 2-3 minutes, stirring frequently, until they start to pop and smell toasty. Transfer to a small bowl to cool.
  5. Make the dressing: In a small bowl or mason jar, combine tahini, maple syrup, apple cider vinegar, and salt. Add 2 tablespoons warm water and whisk or shake until smooth. Add more water if needed to reach a drizzle-able consistency. Taste and adjust.
  6. In a large mixing bowl, combine arugula, roasted squash (cooled slightly), dried cranberries, and fresh apple. Drizzle about half the dressing over the top and toss gently until lightly coated. Add more dressing as needed.
  7. Sprinkle toasted pepitas and crumbled feta or goat cheese (if using) over the top. Serve immediately while the squash is still warm, or at room temperature.

Notes

Don’t skip the single-layer rule for roasting squash to ensure caramelization. Season the squash generously with salt. Toast pepitas in a dry pan and watch closely to avoid burning. Let squash cool slightly before adding to greens to prevent wilting. Dress the salad lightly at first; you can always add more. The dressing thickens as it sits; add warm water to thin if needed.

Nutrition

Keywords: roasted delicata squash, fall salad, cranberry salad, maple tahini dressing, harvest salad, vegetarian, gluten-free

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