Place a rack in the center of your oven and preheat the oven to 425 degrees F. Halve the butternut squash, scoop out the seeds, then arrange the halves on a baking tray, cut sides up. Drizzle with 1 teaspoon olive oil and sprinkle lightly with salt and pepper. Bake 45-55 minutes, just until the squash is fork tender. Remove from the oven and let cool. Reduce the oven temperature to 375 degrees.
While the squash is baking, place the broth in a small saucepan and bring to a boil. Add the quinoa, return to a boil, then reduce the heat, cover, and let simmer for 12 minutes, until most of the broth is absorbed. Remove from the heat and let sit, covered, for 15 minutes. Fluff with a fork, then set aside.
In a large skillet, heat the remaining 1 teaspoon olive over medium. Add the kale and cook until wilted, about 4 minutes, then reduce the heat to medium low. Add the garlic, oregano, 1/2 teaspoon salt, and 1/2 teaspoon black pepper. Cook 30 additional seconds, until is fragrant. Stir in the chickpeas, orange zest, orange juice, cooked quinoa, and cranberries.
Once the squash is cool enough to handle, scoop out the flesh, leaving a 1/2-inch-thick border around the sides and a 3/4-inch border along the bottom. Reserve the flesh for another use (or if you don’t mind a super duper stuffed squash, mix it in with the rest of the filling). Stuff the kale quinoa filling into the squash halves, then return the squash to the oven. Bake at 375 degrees until hot, about 10 additional minutes. Serve warm.