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large white plate with salad with radicchio, watermelon radish, sliced acorn squash, chopped apple and chopped cilantro, with one wooden salad spoon to the top left

Roasted Squash and Chicory Salad (AIP, paleo, vegan, Whole30)

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This Roasted Squash and Chicory Salad is made with tender acorn squash, bitter chicory, sweet and crunchy apple, watermelon radish and an herbed balsamic vinaigrette. It’s AIP, paleo, vegan and Whole30 compliant.


  • 1 small acorn squash (approximately 2 pounds)
  • 2 TBSP olive oil
  • sea salt
  • 1 small head radicchio, chopped
  • 1/4 cup cilantro, chopped
  • 2 watermelon radishes (or substitute with another mild radish variety e.g. Snowball, Purple Plum or White Icicle), thinly sliced*
  • 1 apple (any variety), finely diced

Basil Balsamic Dressing

  • 1/2 TBSP basil, finely chopped
  • 1 clove garlic, crushed
  • 1/4 cup balsamic vinegar
  • 1/4 tsp sea salt
  • 1/4 cup extra virgin olive oil


  1.  Preheat your oven to 450F and line two large baking sheets with parchment paper.
  2. Cut the stem off the end of the acorn squash and cut the squash in half lengthwise. Remove the seeds using a spoon and cut the squash into 1/2-inch-thick slices.**
  3. Lay the sliced squash in a single layer onto the baking sheets and coat with olive oil and sea salt.***
  4. Roast squash for 25-30 minutes, flipping once midway through.
  5. Assemble your salad by layering chopped radicchio, cilantro, roasted squash, watermelon radish and apple.
  6. To prepare dressing, crush garlic and finely chop basil. Add to a mason jar or bowl along with balsamic vinegar and salt. Slowly whisk in olive oil until an emulsion is formed.
  7. Toss salad with dressing shortly before serving and more salt to taste.


* I recommend using a mandoline if you have one, otherwise, try to slice as thinly as possible using a very sharp knife.

**Peeling the skin here is optional – acorn squash skin is edible but it’s totally a personal preference.

***Depending on the size of your baking sheets you might use more than two of them. You want to ensure the squash pieces are laid out evenly and separated so that the squash roasts rather than steams.

  • Prep Time: 40 minutes
  • Category: Salads