Preheat oven to 450°F
Peel butternut squash with a vegetable peeler. Carefully cut in half. Scoop out the seeds, discard seeds, and then cut in small cubes. Place in a large bowl.
Wash Brussels sprouts, cut off the stems and peel any loose leaves off. Cut them in half, and any larger sprouts you can cut into fourths. Place in the bowl with the butternut squash.
Add olive oil, salt and pepper and toss to coat.
Spread out butternut squash and Brussels in a single layer on a rimmed baking sheet. Use two baking sheets if veggies seem crowded. (If there are too many Brussels and squash on a pan they can have a hard time crisping up perfectly).
Roast until dark brown and crisp underneath, ~20-25 minutes, and add dried cranberries to the baking sheet about 5 minutes before veggies are done.
While the veggies are cooking, prepare the citrus dressing. Mix all of the ingredients in a small bowl and whisk together.
Place veggies in a large serving bowl. Add in pecans and any more dried cranberries, if desired.
Pour dressing over veggies and toss or serve on the side. Enjoy immediately.