Heat oven to 425°F. On a large baking sheet, layer 1/2 inch sliced acorn squash and carrot slices evenly. Drizzle lightly with olive oil and toss with salt and pepper. Bake for 30 minutes, tossing halfway through cook time.
Meanwhile, cook quinoa according to package directions.
Whisk together olive oil, maple syrup, apple cider vinegar, a healthy amount of black pepper, and salt to taste. Set aside until ready to assemble the salad.
Toss together roasted squash and carrots, quinoa, cranberries, almond slivers, and arugula. Toss with dressing. Salad is excellent served warm or room temperature.