Preheat the oven to 400°F (200°C). Slice the acorn squash into half, and then into wedges, removing the seeds. Place the wedges on a baking sheet, drizzle with a tablespoon of pumpkin oil, and season with salt and pepper. Roast in the oven for 20-25 minutes, or until the squash is tender and slightly caramelized. Once cooled, cut the squash into bite-sized pieces.

While the squash is cooking, in a large pot, bring 3 cups of water to a boil. Add a pinch of salt and the rinsed wheat berries. Reduce heat, cover, and simmer for 45 minutes to an hour, or until the wheat berries are tender but still have a chewy texture. Once done, drain any excess water and set aside to cool.

Heat the pumpkin oil in a medium skillet over medium heat. Add the chopped kale and cook until its wilted. Set aside.

To the skillet of kale, add the roasted acorn squash, cooked wheat berries, dried cranberries, and pepitas. Drizzle the remaining pumpkin oil over the top, and toss everything to combine. Season with salt and pepper to taste.