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.

winter squash salad with kale, basil and pumpkin seeds

Winter Squash Salad with Basil, Kale + Tomato Chili Oil

Roasted, caramelized squash and toasty pumpkin seeds paired with a spicy basil, fresh kale and a homemade, SUPER EASY, tomato chili oil. Sweet, salty, spicy and sassy — this squash salad is all you need to eat during any season.
Course Main Course, Salad, Side Dish
Cuisine Gluten-Free, Healthy, Vegan
Servings 2


  • 2 1/2 cups kabocha squash diced with skin on or off (can sub for butternut, acorn squash, buttercup, or hubbard)
  • Squash seeds washed and drained
  • 3 cups raw kale leaves removed from the stem and chopped or torn into small, bite-sized pieces (if feeding more than 2 people, serve 1 1/2 cups of kale per person)
  • 1/3 cup fresh basil leaves finely chopped
  • Salt for seasoning
  • Olive oil for roasting

Tomato Chili Oil

  • 1 tbsp tomato paste
  • 1/2 tsp salt
  • 1/4 cup olive oil
  • 1 tsp chili flakes or to taste


  • Preheat the oven to 425 degrees F.
  • Combine the tomato chili oil ingredients in a mason jar or bowl and shake or whisk to thoroughly combine. Let the oil infuse as you finish the dish.
  • Cut the kabocha squash into quarters and remove the seeds if you haven't done it already.
  • Wash and drain the seeds, separating them from the stringy, sticky interior of the squash.
  • Toss the seeds in a bowl with a pinch of salt and pepper, if using. Spread the seeds evenly on a sheet pan and roast for 7 minutes. Remove the seeds from the oven once they are golden brown and crispy. Once the seeds are removed, adjust the oven temp to 475 degrees F.
  • While the seeds are roasting, peel the squash with a knife or peeler. Then, cut the squash into small 1-inch(ish) cubes. If using kabocha, you can roast it with the skin on.
  • Toss the squash cubes in a bowl with about 1 tsp of olive oil and a pinch of salt. Spread the squash onto a sheet pan, making sure that no pieces are overlapping and that it's not overcrowded. Roast the squash for 15-20 minutes, until golden brown and tender. If the squash isn't golden brown after 20 minutes, keep going for another 5-10 minutes and check on the squash frequently so it does not burn. If necessary, roast the squash on two sheet pans.
  • While the squash is roasting, combine the basil and kale in a bowl. Add a pinch of salt to season the greens and toss until fully coated.
  • Toss the salad in 2 tsp of the tomato chili oil and add more to taste, if needed. You will be adding a little drizzle on top as well, so make sure your greens are only lightly coated.
  • When the squash is done, add the roasted squash to the salad. It will slightly cook the kale when you toss it, changing the pigment of the kale to a bright green.
  • Put the squash salad onto a plate. Top with the roasted seeds and another drizzle of tomato chli oil. Serve immediiately. If serving with cheese or protein, add those on top before drzzling with more oil and then serve.


Keyword basil, diy infused oil, diy pumpkin seeds, homemade chili oil, kabocha, spicy salad, squash salad, winter squash

7 thoughts on “Winter Squash Salad with Basil, Kale + Tomato Chili Oil”

  1. 5 stars
    This recipe is SOOO GOOD!!! I’ve always been a big fan of kabocha, but never ate it with this taste profile and I will definitely be making it again! It was so satisfying and filling and filled with vegetables! Great fresh out of the oven, hot, as well as cold the next day! The only thing with the leftovers is that the roasted crunchy seeds get a little soft, but can’t complain! Can’t wait to make this again soon! Thank you so much, Skyler!

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