Preheat your oven to 400˚F.
Line a sheet tray or two with parchment paper. Mix together the brussels sprouts, butternut squash, olive oil, salt, and pepper until everything is evenly coated.
Place the trays into the oven and bake for about 20 minutes, stirring halfway through the cooking time. The vegetables should be mostly cooked.
In the meantime, whisk all of the ingredients for the vinaigrette in a small bowl until they have emulsified. Set aside.
After 20 minutes of roasting, mix the walnuts into the vegetables and return the tray to the oven for an additional 5 minutes.
After 5 minutes, remove the tray from the oven. Allow the tray to cool slightly and then add in the cranberries and vinaigrette. Gently mix the vegetables with the vinaigrette so that everything is evenly coated. Enjoy!