RECIPE: Roasted Pears and Delicata Squash with Fall Greens



Fall green salads with warm roasted squash are everywhere now! We’ve bumped it up a notch by adding roasted pears, power-packed kale, and a maple-cider dressing. It’s a good seasonal salad for company or a holiday meal — healthy and easy to make! While the pears and squash are roasting together, prep the salad. Look for all four main ingredients at a fall farmers’ market. Serves 4 to 6.

Find out how to roast the perfect pear here.


1 medium delicata squash, washed, halved, seeded, and sliced into 1/2-inch crescents

olive oil, divided

1 tablespoon maple syrup

3 pears

1 bunch kale, either Italian or curly kale, stems removed and rinsed

1/2 head radicchio, torn into pieces

1/4 head frisee lettuce, if available, torn into pieces 

1/2 cup pomegranate seeds or dried cranberries

1/2 cup walnuts, toasted and roughly chopped

Garnish: Feta, blue, or goat cheese, optional


2 tablespoons apple cider vinegar

1 tablespoon maple syrup

2 teaspoons minced shallots

5 tablespoons olive oil

Two pinches of salt, or more to taste


  1. Preheat oven to 350 degrees. Line two baking sheets with parchment paper.. Place squash crescents on one and drizzle with olive oil to coat. Season with salt. Place in the oven to bake, flipping halfway through, for 25–30 minutes, or until tender. When they come out of the oven, drizzle with 1 tablespoon maple syrup and gently mix to coat the squash pieces. Set aside.
  2. Peel pears, cut in half, and scoop out the core with a spoon. Place on the other baking sheet and rub each pear with olive oil. Place pears cut side down, and bake for about 30 to 40 minutes. The pears should be lightly browned on the cut side and easily pierced with a fork.
  3. While the pears and squash are baking, prepare the salad and make the dressing. Roughly chop the kale and add to a large bowl. Add 2 pinches of kosher salt and drizzle with 1 tablespoon of oil and vigorously toss and massage the salt and oil into the kale with your fingers until well coated and kale leaves are thoroughly softened and tenderized. 
  4. Place the kale in a wide salad bowl along with the radicchio and frisee, if you found some.
  5. Whisk the apple cider vinegar, maple syrup, shallots, olive oil, and salt together in a small bowl. 
  6. Dress the salad with most of the dressing, saving a little. When the pears and squash have cooled for a few minutes, mix in the squash first and then top the salad with the pears. Drizzle the rest of the dressing and garnish with the nuts and pomegranate seeds. You can roast both earlier in the day, but reheat briefly before serving.

Looking for more great roasted pear recipes? Try:

How to Roast a Pear

Fall Baby Greens Salad with Roasted Pears

Roasted Pears with Reduced Apple Cider and Cashew Cream

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Catherine Walthers
Catherine Walthers
Catherine Walthers, Bluedot’s food editor, is a Martha’s Vineyard-based writer, culinary instructor, and private chef. A former journalist, she is the author of 4 cookbooks, including Kale, Glorious Kale, Soups + Sides, and Raising the Salad Bar. She wrote an environmental guidebook called A Greener Boston published by Chronicle Books in 1992. Follow her on Instagram @catherine_walthers.

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