Prep: Preheat the oven to 400F and set two small baking trays aside. Bring a large pot of water to a boil and cook the farro according to package instructions. Drain the farro once tender and set aside.
Roast the Vegetables: On one tray, combine the butternut squash with the maple syrup, rosemary, salt, pepper, and a drizzle of olive oil. Toss well. On the second tray, combine the Brussels sprouts, shallot, and thyme. Season with salt and pepper, drizzle with oil, and toss well.
Bake: Place both baking trays on the top rack of the oven and bake for 20 minutes. Remove the Brussels sprouts after 20 minutes and set aside. Flip the butternut squash and return to the oven for an additional 10 to 15 minutes, until tender with golden edges.
Make the Dressing: Add the olive oil, vinegar, maple syrup, mustard, garlic, and salt to a small jar. Shake well until emulsified and then set aside.
Combine: Add the farro to the large mixing bowl and top with the roasted Brussels and butternut squash, as well as the parsley, cherries, and pumpkin seeds. Pour the dressing over the salad and toss well to combine.
Serve: serve chilled (or warm, if you’d like!) Store leftovers in the refrigerator for up to 3 days.