Preheat the oven to 425°F. Using a sharp knife, cut the squash in half and scoop out the seeds with a spoon. If using acorn or butternut squash, roast the squash in two halves and cut into pieces after it is baked. For Delicata or Kabocha squash, cut the squash into half moon pieces. Brush the squash pieces with one tablespoon of olive oil and sprinkle with salt. Roast for about 20-25 minutes, turning slices once during cooking, or until soft. (The acron or butternut squash will take longer, more like 40 minutes.) When cool enough to handle, cut the large pieces of squash into half-moon pieces.
While the squash is baking, prepare the other ingredients. Rinse the kale, remove the stems, and cut into bite-size pieces. Place the kale in a colander and let air dry.
*You can buy pomegranate seeds in some grocery stores in the produce section. OR you can extract the seeds yourself from a whole pomegranate. Using a sharp knife, carefully cut the pomegranate in half, then in quarters. (Be sure to wear an apron, as the pomegranate juice will stain light clothes.) Fill a medium bowl halfway with cold water and using your fingers, separate the seeds from the membrane and let drop into the water. The seeds will sink to the bottom and the membrane will float to the top. Once you get all the seeds out, remove the white membrane and pour the water and the seeds into a strainer. Dry them off with paper towels and keep in an airtight container for 2 – 3 days.
**To toast the pine nuts, cook them in a dry skillet over medium heat for 4 to 5 minutes until lightly toasted and nutty smelling. Keep a close eye on them, swirling the pan and/or stirring often, as they can quickly burn. OR roast in a 350°F oven for 6 – 7 minutes until lightly browned, stirring them once or twice to make sure they cook evenly. After either method, dump the pine nuts onto a plate to stop the cooking. Let cool.
Whisk the Balsamic vinegar with the remaining 4 tablespoons of olive oil in a small bowl until combined. Season with salt and pepper to taste. Place the kale in a large bowl and toss with half the vinaigrette until evenly coated.
To assemble the salad, arrange the squash slices on a large platter–you can leave the skin on and people can cut it off themselves (though you can eat the Delicata squash skin, FYI)–and drizzle with the remaining vinaigrette. Layer with the kale and sprinkle with pomegranate seeds, pine nuts, and Parmesan shavings (use a vegetable peeler and a chunk of Parmesan).
