Preheat your oven to 425°F (220°C).

Peel the butternut squash carefully using a vegetable peeler. Cut it in half lengthwise and scoop out the seeds.

Chop the squash into roughly 1-inch cubes for even roasting.

In a large bowl, toss the squash cubes with olive oil, cinnamon, salt, and pepper until evenly coated.

Spread the squash in a single layer on a baking sheet, making sure the pieces aren’t crowded.

Roast for about 25-30 minutes, flipping halfway through, until the squash is tender and caramelized around the edges.

Pro Tip: Don’t skip flipping the squash halfway—it ensures all sides get that beautiful golden color and even cooking.

While the squash roasts, wash the kale thoroughly and dry it well. Remove the tough stems and chop the leaves into bite-sized pieces.

Place the kale in a large mixing bowl.

To soften the kale and reduce bitterness, drizzle with about 1 tablespoon of olive oil and a pinch of salt. Massage the leaves with your hands for 2-3 minutes until they start to soften and darken.

Set aside while you finish roasting the squash.

Pro Tip: Massaging kale makes it much more tender and enjoyable to eat raw—don’t rush this step!

In a small bowl, whisk together the olive oil, apple cider vinegar, maple syrup (or honey), Dijon mustard, salt, and pepper.

Whisk continuously until the dressing emulsifies and becomes slightly thickened.

Taste and adjust seasoning if needed—add more vinegar for tang or maple syrup for sweetness.

Once the squash is done roasting and slightly cooled, add it to the bowl with the massaged kale.

Toss in the toasted pumpkin seeds or walnuts and dried cranberries or pomegranate seeds, if using.

Drizzle the dressing over the salad.

Toss everything gently but thoroughly to combine all the flavors evenly.

Finally, sprinkle crumbled feta or goat cheese on top if you like a creamy finish.

Serve the salad immediately for the best texture and flavor.

This salad also holds up well if refrigerated for a few hours, making it a great make-ahead option.