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Roasted Winter Squash with Kale & Pomegranate Seeds

Though you can use any winter squash for this recipe, Delicata is both beautiful and practical — unlike with other varieties, you can actually eat the skin.
Cook Time40 mins
Course: Salad, Side Dish
Cuisine: American
Keyword: delicata squash, kale, pomegranate, roasted vegetables, winter, winter squash
Servings: 4
Calories: 253kcal
Author: Anna Watson Carl


  • 1 pound winter squash such as acorn, butternut, delicata, or kabocha
  • 5 tablespoons extra-virgin olive oil divided
  • Fine sea salt and freshly ground black pepper
  • 2 tablespoons balsamic vinegar
  • 1 bunch Tuscan Lacinto kale stems removed, cut into bite-size pieces
  • 2 tablespoons pomegranate seeds
  • 2 tablespoons toasted pine nuts
  • Shaved Parmesan* for garnish (*Eliminate the Parmesan for a dairy-free, vegan salad.)


  • Preheat the oven to 425°F. Line a baking sheet with aluminum foil.
  • Use a sharp knife to cut the squash in half then scoop out the seeds with a spoon. If using acorn or butternut squash, place the 2 halves, cut-side up, on the foil-lined baking sheet. If using delicata or kabocha squash, cut it into half-moons and arrange those on the foil-lined baking sheet. Brush the squash with 1 tablespoon of the olive oil, sprinkle with salt and pepper, and roast until soft (turn the delicata or kabocha squash once during roasting), about 20 to 25 minutes for the delicata or kabocha squash and 40 minutes for the acorn or butternut squash. Cool slightly. When cool enough to handle, cut the acorn or butternut squash into half-moon pieces.
  • Pour the balsamic vinegar into a small bowl. Add the remaining 4 tablespoons olive oil in a slow, steady stream, whisking constantly. Season to taste with salt and pepper.
  • Place the kale in a large bowl, add half the vinaigrette, and toss until evenly coated.
  • To assemble the salad, arrange the squash slices on a large platter – you can leave the skin on and people can cut it off themselves and drizzle with the remaining vinaigrette. Arrange the kale on top then sprinkle with pomegranate seeds, pine nuts, and shaved Parmesan


Do Ahead: The squash can be roasted ahead and kept at room temperature for several hours before using. Alternatively you can roast the squash 1 day ahead and keep it in an airtight container in the refrigerator for up to 1 day. Bring it to room temperature before using.
*Eliminate the Parmesan for a dairy-free, vegan salad.

Used with permission from The Yellow Table: A Celebration of Everyday Gatherings: 110 Simple & Seasonal Recipes by Anna Watson Carl, Sterling Epicure, an imprint of Sterling Publishing Co., Inc., 2015. Photography by Signe Birck