Preheat oven to 425 degrees F. Grab a large baking sheet with sides.
Peel, remove seeds, and dice your butternut squash. Cut the ends off each Brussels sprout, then slice in half lengthwise. Place on the baking sheet. Drizzle avocado oil. Sprinkle with salt. Mix with your hands or a large spoon. Arrange evenly on the baking sheet. Bake for 25 - 30 minutes or until brown and soft.
Boil water and cook pasta according to directions.
Devein the kale. Gather the kale leaves into a bunch. Slice very thinly across the kale to make thin strips. Place kale in a large bowl.
Once the pasta is cooked, drain the pasta and dump the warm pasta onto the kale in the bowl. This will help wilt the kale.
Add the cooked, shredded chicken to the bowl with the pasta and kale.
Once the butternut squash and Brussels sprouts are cooked to your liking, add them to the bowl as well. Add the tart cherries, pepitas, and pecorino romano cheese.
Combine all the dressing ingredients into a mason jar. Securely screw on the lid and shake well.
Pour the dressing over the salad. Toss together with two large spoons.