Toast the bread: preheat the oven to 300°F. Cube the bread into ~1 inch bite sized cubes. Place on a baking sheet, toss with 1-2 Tbsp. olive oil and toast for 15-20 minutes.
Roast the butternut squash: Increase the oven temperature to 375°F. Place cubed butternut squash on a baking sheet. Toss with 1/2 tsp. salt, 1/2 tsp. pepper and 1-2 Tbsp. olive oil. Spread evenly on pan. Bake until fork tender, ~35 minutes. Set aside to cool.
Massage the kale: Pull the kale leaves off from the stems and discard the stems. Use a chef’s knife to chop the kale into small, bite-sized pieces. Transfer the kale to a big bowl. Drizzle olive oil generously over the kale and use your hands to massage the kale leaves (lightly scrunching big handfuls at a time, until the leaves are darker in color). About 2 minutes.
Make the dressing: In a bowl or measuring cup, whisk together all of the ingredients for the dressing.
In a large salad bowl, combine the arugula, kale, apples, pecans, feta, dried cranberries, butternut squash and bread together. Serve with dressing on the side or toss dressing in the salad if serving immediately.
Toast the pecans if preferred: Preheat the oven to 350°F and spread the pecans on a baking sheet. Toast them until lightly golden and fragrant, about 5 to 10 minutes, tossing them once or twice to make sure they bake evenly. Remove the tray from the oven and set them aside to cool.Instead of toasting the bread cubes, you can also dry them if you plan ahead: Spread the bread cubes over a baking sheet. Leave uncovered overnight to stale and harden. When ready to make the salad, you won't have to toast them!