Preheat the oven to 400º F. Cut the acorn squash in half; and cut one half of the squash in half again. Reserve the remaining squash for another purpose. Scrape out the seeds with a spoon, and slice the squash in 1/2" thick slices. Toss in just enough olive oil to coat them, and place on a baking sheet. Lightly salt.
Roast for 15 minutes, or until just tender. Remove from the oven and set aside.
While the squash is roasting, make the caramelizing sauce by combining the brown sugar, butter and water together in a small sauce pan over medium heat. Continue to heat until the butter is melted and the brown sugar dissolves into the water and butter. Reduce the heat and simmer for 20 seconds.
Dip the squash pieces in the caramelizing sauce to coat, and place them back on the baking sheet. Move the oven rack up to the top rung, or the rung you use for broiling, and turn on the broiler. Put the squash back in the oven and broil for 5 minutes. Remove and allow to slightly cool while you make the rest of the salad.
Place the kale on a workspace, lightly salt, and massage the kale until it becomes slightly limp and very moist. Dry by squeezing it with paper towels and place in a bowl.
Cut the apple in quarters, remove the core, and slice thinly. Place in the bowl with the kale. Add a handful or two of pumpkin seeds, and then the caramelized squash slices.
Combine the honey and apple cider in a bowl, and mix with a fork to completely dissolve the honey into the apple cider. Drizzle half of it over the kale salad and lightly toss, being careful not to break up the squash pieces. Add more dressing as desired.