Preheat oven to 400 degrees F.
Line baking sheet with foil and grease with cooking spray.
Toss cubed squash cubes with olive oil, maple syrup, balsamic vinegar, garlic, and salt and lay out on prepared baking sheet.
Roast in preheated oven for 40 minutes.
Let cool.
Make the dressing by coming all dressing ingredients in a lidded jar and shaking until well combined.
Add kale to a large bowl and drizzle with dressing. Massage the dressing into the kale leaves for about 1 minute, until all kale is covered and slightly softened from the dressing.
Top kale with squash, goat cheese, pepitas, and cherries.
Serve and enjoy!
This salad will keep in the refrigerator about 1-2 days, as kale will not wilt like most softer greens.