Winter. It’s basically here already. And this El Nino dude is kicking our butts up here with some crazy rain. I keep looking around to see if any animals are walking two by two towards a really big boat. When this time of year hits, I want comfort food, of course, but I also want something bright and fresh. So I looked for the cheeriest things I could find that also happened to be in season and turned it into this winter kale salad. The squash even smiles. Wait…what? Just keep reading, you’ll see.
First up, sunny squash. Remember our good friend Delicata? I do love it so. It’s the only winter squash I know of with skin that is thin enough to eat after cooking. Good thing, too, because I have no idea how you would peel it without losing a ton of the flesh. I love the little bumpy shape it makes when cut in half lengthwise and then sliced across into half-moons.
Before you get to cutting, preheat the oven to 400F, because we’re going to roast these little beauties up before adding them to the salad.
Then, slice the squash in half down the length, scoop out the seeds, and place each half cut-side down before cutting across to make little half-moons. Vida calls them squash smilies. See, I told you it would make sense. Have fun arranging the smiling squash semi-circles onto the baking sheet – it reminded me a bit of Tetris. This is a great opportunity to get your kids involved in the salad-making process.
Next up, the dressing! I had a bunch of those little mandarin oranges called Cuties, and just knew they would make a bright, zippy vinaigrette. Two or three of the baby oranges, a splash of rice wine vinegar, a tablespoon or two of olive oil, and a drizzle of maple syrup, and you’re in business! Oh, don’t forget a pinch of salt to bring all the flavors out big and bold. I love to shake up dressings like this in a little mason jar – also a fun thing for the kiddos to do.
After the dressing is all mixed up, massage it into the kale – you can get pretty aggressive, the kale can take it. Ideally you would do this as soon as the squash starts roasting, so the kale has a little bit of time to tenderize. This is one of the only kinds of salads where it actually stays good in the fridge after being dressed – in fact, sometimes it’s even better after sitting for a day or two.
Next, some toasted almonds add a bit of crunch and nutrition. The nice thing about this is you can toast the almonds in the oven at the same time that the squash is roasting – just be careful not to burn them. Been there, done that. A lot.
Is there anything more beautiful than pomegranate pearls? They really look like little jewels! Every December I look forward to pomegranate season, and I recently discovered that Vida can eat a whole pom’s worth of pearls in one sitting. I’ll take that over jelly beans any day!
Now it’s time to put it all together. Top the dressed kale with a few squash slices (or smilies, if you prefer), a handful of almonds, and a sprinkle of pomegranate pearls. If this salad doesn’t brighten up your day, you might want to look into that light therapy stuff. I mean, just look at it. It’s like happiness in a bowl! Ok, I might be taking this too far, we’re talking about a kale salad here. But really, this salad has some serious power against the winter doldrums.
By the way, if you’re just not a kale person, I’m confident that this would be equally tasty using another variety of dark leafy greens – rainbow chard comes to mind! 🙂 Hmmmm….that’s a really good idea.
So what do you think? Will you give this a go? Let me know in the comments! And, if you do make this, please take a picture of your creation and share it on Instagram with the tag #eatwithinyourmeans. I love seeing your kitchen adventures!
Here’s to winter! We’ll get through it, one salad at a time.

Winter Kale Salad
Ingredients
- 2 bunches of curly kale (washed and chopped)
- 1 delicata squash (seeds removed and cut into 1/2" thick half-moons)
- 1/2 cup slivered almonds
- 1 pomegranate (seeded)
For the vinaigrette
- 2-3 cup mandarin oranges (juiced (about 1/2 ))
- 1 Tablespoon rice wine vinegar
- 2 Tablespoons olive oil* (optional)
- 1 Tablespoon maple syrup
- 1/4 teaspoon salt
Instructions
- Preheat oven to 400F
- Wash and prep the delicata squash by cutting it lengthwise and then cross-wise into 1/2" thick half-moons
- Place squash slices on a baking sheet in a single layer
- Roast squash for 20 minutes until tender
- After 10 minutes of time has elapsed, place the almonds in the oven on a small sheet pan, checking often to make sure they don't burn
- Remove the squash and almonds from the oven and let cool
- Meanwhile, add the vinaigrette ingredients into a small container with a lid and shake vigorously until well-combined
- Pour dressing over kale in a large bowl and massage into the kale
- Divide the salad into portions and top each serving with squash slices, pomegranate pearls, and toasted almonds.
- Leftover salad keeps well in the refrigerator for up to 4 days.
This sounds so so delicious. I am a big fan of kale all year round. This is gorgeous with all the colours too.
Love from Trinity (England)
Thank you Trinity! 🙂 I love me some kale too, no matter the season.
This salad is so gorgeous! It would be perfect on a holiday table!
Thanks, Jenn! It just looks like Christmas to me. 🙂
That’s just too funny…I think I’m calling it squash smilies from now on. ? As for burning almonds, I’m right there with you. I am a chronic almond burner. So much so that I’ve developed various cooling strategies for saving nearly too-far-gone almonds.
And this salad! It has so many of my current fav flavors, and *gasp* (this never happens to me) I think I actually just so happen to have everything for this salad except the kale. ? Add to that the fact that we all adored and *devoured* your other salad, and this definitely is happening. Probably using some of those going south avocados down in the bottom fridge drawer…(which, BTW, that avocado as part of massaging the kale is just genius! It’s like magic, of the most delicious variety!)?
The salad is so beautiful, it’s a shame to eat it. But we did! Yum!
Wow, all of my favorite things in one salad bowl! I love the combination of hearty squash and kale with the citrusy zing of the oranges and pomegranate. That’s quite the vitamin C bomb too, I can almost feel my immunity doing a happy dance 🙂
This looks like such a beautiful Winter salad! I love your food styling as well!
Gorgeous colors. Looks good enough to eat off the screen!
This salad looks so good, Beth! I love the photos, too – especially of the pomegranate and the almonds. Noms!
Thanks, my sweet friend! 🙂 I’m taking my photography tips from you.
I am making this Monday Evening , with extras for lunch! I love all of the individual ingredients, marinated together, Lovely!
I can’t wait to hear how you like it, Regina! 🙂