Peel, scoop out seeds, and cube butternut squash.* Toss in 2 tbsp extra virgin olive oil, cinnamon, 1/4 tsp salt, and 1/4 tsp ground pepper. Spread on baking sheet and roast for 30 minutes at 400°F, or until squash is tender and golden brown.
In a medium skillet over medium heat, toast walnuts until golden brown and fragrant.
Combine kale, farro, apples, squash, walnuts, cheese, and cranberries in a bowl.
For the dressing, whisk 1 tbsp olive oil, orange juice, mustard, shallot, 1/4 tsp salt, and 1/4 tsp pepper in a bowl until fully combined.
Dress salad immediately, or keep dressing on the side and dress your salad as you go.
*Skip this step and buy cubed butternut squash if you prefer