Preheat the oven to 400 degrees F. Place the butternut squash on a sheet pan, drizzle olive oil and maple syrup, and season with salt and pepper. Toss to coat, then roast the squash for 15 to 20 minutes, turning once, until tender.
Bring 2 1/4 cups water and 1/2 teaspoon salt to a boil. Add freekeh, cover, and reduce heat to medium-low. Simmer until all liquid is absorbed, about 20 minutes. Remove from heat and let stand, covered, for 5 minutes. Fluff with a fork and set aside.
In a large sauté pan, heat 1 tablespoon olive oil over medium, then add the kale. Cook and stir until wilted, about 5 minutes. If all of the kale will not fit in your sauté pan, add it slowly as it cooks down. Stir in the garlic, salt, pepper, nutmeg, and crushed red pepper and cook 1 additional minute.
Next, make the dressing. Whisk together the apple cider vinegar, maple syrup, orange juice, Dijon, salt, and pepper until combined. While whisking, slowly pour in the olive oil and continue stirring until well incorporated. (Alternatively, you can shake all of the ingredients together in a mason jar.)
Finally, assemble the salad. Stir the freekeh, butternut squash, cranberries, and walnuts into the skillet with the kale. Pour enough of the dressing to nicely moisten the mixture over the top, toss gently to coat. Transfer to serving plates and drizzle a little more dressing over the top. Serve warm or at room temperature.
TO STORE: Leftover Maple Roasted Butternut Squash Freekeh Salad with Kale can be stored in the refrigerator in an airtight container for up to five days.
TO FREEZE: Freezing the leftovers of this freekeh salad is definitely possible. Note that the vegetables may lose some texture. For best results, I recommend omitting the dressing and cranberries on portions that will be frozen. Add them once defrosted and ready to serve.