Preheat the oven to 425 degrees F (220 C). Place cubed squash and garbanzo beans on a sheet pan. Drizzle with 1 tablespoon of olive oil, sprinkle with kosher salt. Place garlic cloves in the center of a small piece of foil. Drizzle with a tiny bit of olive oil and fold it up into a little packet. Place the packet on the sheet pan. Roast everything for 30-40 minutes, until squash is tender.
While vegetables roast, prepare the dressing. In a small bowl, whisk together the olive oil, 2 tablespoons lemon juice, 1/2 teaspoon kosher salt, 1/4 teaspoon black pepper, and 1 teaspoon sugar. When the sheet pan comes out of the oven, carefully open the foil packet, mash up the roasted garlic cloves into a paste, and add it to the dressing. Whisk well to combine.
In a large bowl, drizzle the chopped kale with about 3 tablespoons of the prepared dressing. Use your hands to massage the dressing into the kale for 2-3 minutes, until the kale becomes deep green, softer, and more tender.
Place the massaged kale in a large salad bowl. Top with the roasted squash and garbanzo beans. Arrange the sliced honeycrisp apple pieces decoratively on the salad.
Dot the whole salad with the pepitas and dried cherries.
Finish the salad with the remaining roasted garlic dressing. Serve warm or cold, as desired.