Preheat the oven to 375 degrees F (190 degrees C).
Stir 2 tablespoons olive oil and cinnamon together in a cup. Place squash on a baking sheet and brush with the cinnamon oil on both sides of each slice.
Roast in the preheated oven until squash is soft and starting to brown at the edges, 30 to 40 minutes.
Meanwhile, combine 1/2 cup olive oil, maple syrup, vinegar, and mustard in a jar, close, and shake well. Set dressing aside.
Combine kale, red cabbage, cranberries, and walnuts in a large bowl. Season with salt and pepper to taste. Pour dressing on top and mix well or massage with your hands. Mix in apple slices.
Arrange the roasted squash slices around the salad and serve.
