Preheat oven to 425 degrees. Line a sheet pan with parchment paper and set aside.
Cut off ends of delicata squash then cut it in half, lengthwise. Scoop out seeds then cut into slices about ¾-inch thick.
Place squash slices in a large bowl then drizzle with one tablespoon olive oil and sprinkle with sea salt and black pepper. Toss until evenly coated.
Spread out squash slices onto prepared sheet pan then roast for about 15 minutes. Flip slices over then continue roasting for another 15 minutes or until both sides are caramelized.
Preparing the Salad
Meanwhile, combine all orange maple vinaigrette ingredients in a bowl and whisk until uniform. Pour dressing over top of chopped kale and massage into the leaves.
Add kale to a large salad bowl, followed by dried cranberries, walnuts, gorgonzola cheese, and pepitas. Toss and mix all ingredients until evenly distributed.
Lay slices of delicata squash over top of salad and serve.
Notes
PreparationMake this salad up to one day ahead of time for one less thing to do on the day of dinner, especially a holiday dinner.ServingServe the salad cold or at room temperature. Serve the dressing separately but alongside the salad so that everyone can control the amount they use or for massaged salad, serve already tossed and massaged in dressing.StorageStore the salad in an airtight container in the refrigerator. It will keep for up to four days.