Preheat oven to 400°.
Peel and cube the butternut squash into 1-inch pieces. Trim and halve the Brussels sprouts, then thinly slice the red onion. Spread the vegetables onto a large baking sheet, drizzle with 2 tbsp. olive oil, and season with salt and pepper. Toss to coat.
1 medium butternut squash, 1 16 oz. bag brussels sprouts , 1/2 cup red onion, 1 tsp salt, 1 tsp black pepper
Cut the bread into 1-inch cubes. In a large bowl, toss with the melted butter, olive oil, garlic powder, salt, and pepper until evenly coated. Spread onto a second baking sheet.
1/2 pound italian bread, 3 tbsp butter, 1/2 tsp. garlic powder
Bake both pans at 400°F. Roast the vegetables for 20–25 minutes, stirring halfway through, until tender and lightly caramelized. Bake the croutons for 15–20 minutes, stirring halfway through, until golden brown and crisp. Let both cool to room temperature.
In a mason jar or small bowl, combine all of the vinaigrette ingredients. Shake or whisk until well combined.
1/2 cup olive oil, 3 tbsp. balsamic vinegar, 1/2 tsp. dijon mustard, 1/2 tsp. salt, 1/4 tsp. black pepper
Core and dice the apple into bite-sized pieces. In a large serving bowl, combine the roasted vegetables, apple, and vinaigrette, tossing to coat. Fold in the garlic croutons, goat cheese, and dried cranberries.
4 oz. goat cheese, 1/2 cup dried cranberries
Let the salad rest for 10–15 minutes before serving so the bread can absorb some of the vinaigrette.