Winter Squash Salad with Basil, Kale + Tomato Chili Oil

Well, if you couldn’t tell by the name of it, this dish a literal MOUTHFUL. I call this my “sassy squash” salad because it totally has an attitude: it’s spicy, sweet, earthy, salty, nutty and just overall surprisingly flavorful. However, I wasn’t going to name it Sassy Squash in my blog post title because I don’t think the word “sassy” makes anyone hungry. So, here we are. This winter squash salad with basil, kale and tomato chili oil will 100% exceed your winter squash expectations. You can use any kind of nutty winter squash (acorn squash, kabocha or butternut,) however I went with a kabocha. I roasted it until caramelized and tender and I also roasted the seeds to use for topping, because food waste is not cool. Then, I paired the squash with a spicy basil, fresh kale and a homemade, SUPER EASY, tomato chili oil. And that’s it. That’s the dish. You can serve it as a side, a veggie base for a protein, or with a fried egg. In this case, I topped it with some pan-seared halloumi because you guys know I love the creamy, saltiness of halloumi with a hint of sweetness and spice (cue my pumpkin spice halloumi recipe from last fall)


  • Kabocha
  • Butternut
  • Acorn
  • Buttercup
  • Hubbard


  • Spaghetti Squash
  • Zucchini
  • Summer Squash

Another example of when I paired a rich, nutty squash with brighter flavors is when I made my steak with chimichurri and a bright, zesty squash side salad. I made that dish during the seasonal transition from summer to autumn, and I’m making this one during that winter to spring transition. The difference here is that this recipe is much more spicy and well-rounded. You can enjoy this during any time of the year, not just during the warm seasons.

Full tutorial (including searing the halloumi) is above. The recipe below is for the squash salad without the halloumi. It’s really funny because “halloumi” has autocorrected to helium every single time when writing this post, so if there are any typos in here that I didn’t catch that are suggesting you sear helium, please do not do that.

5 from 7 Reviews


Adjust Servings
2 1/2 cups kabocha squash
Squash seeds
3cups raw kale leaves
1/3cup fresh basil leaves
Olive oil
Tomato Chili Oil
1tbsp tomato paste
1/2tsp salt
1/4cup olive oil
1tsp chili flakes