Preheat oven to 450F or 425F convection. Line two baking sheets with parchment paper. Add the squash to one baking sheet, drizzle with oil, and sprinkle the spices, salt, and pepper all over. Use your hands to toss to coat thoroughly and spread out into an even layer.
Form the sausage into ping-pong ball sized meatballs or just tear it into chunks and nestle them into the squash. Bake for 25 minutes, or until squash is caramelized and sausage is browned.
On the other baking sheet, add the nuts, oil, maple, spices, and salt. Bake for 4-5 minutes, or until fragrant and bubbling. Remove and let cool while the squash and sausage continue to bake.
In a jar with a lid, add the dressing ingredients and shake vigorously to combine. Add about 2 cups of radicchio to each bowl and toss with a drizzle of the dressing (use about half and save the rest for drizzling on top). Top with squash, sausage, and apple. Drizzle the remaining dressing all over each bowl. Top with nuts, cheese, and herbs (if using).