To make the salad, you will need:
Preheat oven to 425°F. Then prep your squash. First, cut the stem and about a 1/2-inch off the top of each squash.
Stand the squash up, cut side-down, and slice it in half, lengthwise.
Use a spoon to scrape out the seeds
Once you've scraped the seeds out of all four halves, throw the seeds away.
Lay a squash half cut side-down on the cutting board then slice it crosswise into slices about 1/2-inch thick.
Repeat with all of the squash.
Line two large rimmed baking sheets with parchment paper, and pour 1/2 tablespoon olive oil on each.
Divide the squash between the two trays, and toss it around so that it's all coated in oil. Season with salt.
Roast in the preheated oven for 40 minutes, flipping the squash halfway through, until it's soft and browned.
To make the vinaigrette, first thinly slice the shallots.
Squeeze the juice of half a grapefruit into a bowl. You don't need to strain it, but fish out any seeds.
Add the apple cider vinegar, honey, some kosher salt and freshly ground pepper, and vigorously whisk everything together.
Add the oil in a slow, steady stream, continuing to whisk vigorously the entire time.
Once you've whisked the vinaigrette together for about 30 seconds so that it's emulsified, add the sliced shallots.
Transfer the vinaigrette to a smaller bowl or container, and refrigerate until you're ready to serve.
To prepare the kale, first cut off the leafless stem ends.
Use your hands to tear the leaves off of the woody stem that goes down the middle.
You only need the leaves. Throw the stems away.
Repeat with all the kale, until you have a humungous pile of leaves.
To slice your kale, first stack 4-5 leaves on top of each other.
Roll them up as tight as you can.
Slice your kale thinly, into 1/4-inch strips.
Repeat until you've sliced all the kale.
Transfer your kale to a bowl, and refrigerate until you're ready to assemble (and serve) the salad.
RIGHT BEFORE you're ready to serve the salad, put the kale in a large serving bowl, then pour on the vinaigrette and massage it into the kale for about a minute. Add the roasted squash and pomegranate seeds, then toss everything together and serve.
Kale Salad with Roasted Acorn Squash, Pomegranate, and Grapefruit Vinaigrette
For the salad:
2 small acorn squash
1 tablespoon olive oil
kosher salt and freshly ground pepper
3 bunches kale
1 cup pomegranate seeds
For the vinaigrette:
1 tablespoon apple cider vinegar
juice of ½ grapefruit (to yield ¼ cup)
1 tablespoon honey
kosher salt and freshly ground pepper
¼ cup olive oil
2 medium shallots, thinly sliced (optional)
1. Preheat oven to 425°F. Line two large rimmed baking sheets with foil or parchment paper.
2. To prepare acorn squash: Slice the stem and about 1/2 inch off the top of each squash, then slice each squash in half lengthwise and use a spoon to scoop out and discard the seeds and any stringy flesh clinging to the seeds. Place the squash halves cut-side down on the cutting board, and cut each one into slices ½-inch thick crosswise. Pour 2 tablespoons of oil on the parchment paper on each baking sheet then divide the squash slices between them. Season the slices with kosher salt and toss them around to coat them in the oil, then spread them out for roasting, being sure not to crowd them. Roast for 20 minutes, then remove squash from the oven, flip the squash slices, return to the oven, and roast until soft and lightly browned, about 20 minutes more. Let the squash cool to room temperature before assembling the salad. If you're not serving the salad until later, you can store the cooled squash in an airtight container in the fridge.
3. While the squash is roasting, prepare your vinaigrette: In a medium mixing bowl, combine apple cider vinegar, grapefruit juice, honey, a generous pinch of salt, and freshly ground pepper. Whisk vigorously, and continue to whisk as you add the olive oil in a slow, steady stream. After you've added all of the olive oil, continue to whisk until the vinaigrette is fully emulsified. (The oil and the grapefruit juice/vinegar mixture should be combined into one liquid, not separated.) Add the sliced shallots to the vinaigrette, if you're using them, then refrigerate until you're ready to assemble the salad.
4. To prepare the kale, first cut all of the the woody stems off of the bottom. Then, use your hands to tear the soft leaves off of the stem that goes down the middle of each leaf. Throw the stems away, so that all you have left are the soft leaves. To slice the kale, stack 4-5 leaves on top of each other, then tightly roll the stack of leaves. Use a knife to thinly slice the stack of kale, so that you're left with thin ribbons. Transfer the sliced kale ribbons to a large bowl and refrigerate until you're ready to assemble and serve the salad.
5. When you're ready to serve the salad, put the sliced kale in a very large serving bowl. Add the vinaigrette and use your hands to massage the vinaigrette into the kale for about a minute, until the kale has started to soften. Add the pomegranate seeds and roasted squash and toss to combine.
If you’re bringing this salad to a potluck, here’s what to do:
Before the potluck, follow steps 1-4 in the recipe above to prep the salad ingredients, up to a day in advance. Store the sliced kale ribbons in the bowl you plan to serve the salad in, covered with plastic wrap in the fridge. Store the roasted squash with the pomegranate seeds in a separate airtight container, and the vinaigrette in a third airtight container or bottle.
At the potluck, don't assemble the salad until right before you're ready to serve it. To serve, add the vinaigrette to the kale ribbons in the serving bowl, and massage the vinaigrette into the kale for about a minute, until the kale has started to soften. Add the pomegranate seeds and roasted squash and toss to combine.
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