Turn oven to broil on high. Half your head of radicchio, then cut each half into quarters, making 8 wedges total. Place on a rimmed baking sheet, drizzle with 1 tablespoon olive oil, and salt and pepper. Place under the broiler for 5-10 minutes (depending on your broiler) just to achieve a slight char (like you grilled it). Remove from oven. Set aside on a dish or cutting board to cool. When cool enough to handle, chop or slice for your salad.
Adjust oven to 375 F. On the same baking sheet, toss the butternut squash with 1 tablespoon olive oil, salt and pepper. Bake for 40 minutes, tossing at the half way point.
To assemble, layer the salad starting with the radicchio. Drizzle radicchio with a bit of balsamic vinegar. For the next layer, add the butternut squash, then drizzle balsamic. Top with apples and a bit more balsamic. Finally, garnish with Quick Honey Candied Pepitas and serve!
Recipe by Laughter and Lemonade at https://www.laughterandlemonade.com/roasted-radicchio-and-butternut-squash-salad/