Preheat oven to 400 degrees. Chop delicata squash in half lengthwise then scoop out the pulp and seeds. Then slice each half into 1/2 inch pieces. Place squash onto a cookie sheet lined with foil and toss with 1 tablespoon of oil and some salt and pepper. Lay them in one even layer and roast for 20 minutes, flipping them over halfway through.
For the vinaigrette: In a small bowl whisk together 1 tablespoon olive oil, red wine vinegar, mustard and salt and pepper to taste.
On a plate toss together the kale with 1-2 tablespoons of the vinaigrette, then top with squash, remaining vinaigrette, pine nuts & dried cherries.