Preheat oven to 425 degrees. Toss squash with olive oil, salt and pepper and place on baking sheet in one even layer. Bake 10 minutes, turn and bake another 10 minutes until browned and soft. Remove from oven and set aside.
Rinse wheat berries in cold water. Drain. Place wheatberries + water into small saucepan and sprinkle with salt. Cover and bring to boil. Reduce to simmer and cook covered for 45-50 minutes or until cooked. These will usually stay pretty chewy, fyi.
In a large serving bowl, toss kale, feta, pistachios, craisins, roasted squash and wheat berries together with my favorite salad dressing. Serve.