Preheat oven to 425 degrees F. Line sheet pan with parchment paper or foil.
Place squash on baking sheet, add oil, salt, and pepper and toss together.
Bake squash and foil wrapped beets in oven for 30 minutes. Toss squash halfway.
Remove squash and set aside. Check beets; depending on size, may need 10 to 20 more minutes.
Remove beets and allow to cool for 10 to 20 minutes. Remove foil and, under running cool water, gently peel off skin with fingers.
Dice beets.
In a bowl, add squash, beets, and farro.
In a separate bowl, add dressing ingredients and whisk together well.
Add half dressing to bowl with squash and toss together well. Add pumpkin seeds and cranberries and mix throughout.
Serve with remaining dressing on the side.