Preheat your oven to 400°F (200°C).
Prepare the butternut squash by peeling and dicing it into 1-inch cubes. Toss with 1 tablespoon of olive oil, salt, and pepper, then spread in a single layer on a baking sheet.
Roast the squash in the preheated oven for 25-30 minutes, or until tender and lightly browned.
While the squash roasts, prepare the kale by washing, drying, and tearing the leaves into bite-sized pieces. Place in a large bowl.
Segment the orange, removing any seeds and pith. Set aside.
Prepare the dressing: in a small bowl, whisk together the remaining olive oil and apple cider vinegar until emulsified. Season with salt and pepper to taste.
Once the squash is roasted, let it cool for a few minutes before adding it to the kale bowl.
Add the orange segments, dried cranberries, and walnuts to the bowl with the kale and squash.
Drizzle the dressing over the salad and gently toss to combine, ensuring everything is evenly coated.
Serve immediately, or allow the salad to sit for about 10 minutes to let the flavors meld together before serving.