Preheat the oven to 400 F. Peel the carrots. You can chop the carrots into 1 inch pieces or leave them whole. Cut the acorn squash into eighths, then into 1/4" slices.
Transfer the carrots and squash to a baking sheet and toss with olive oil, salt, and pepper. Transfer to the oven and cook for 15-20 minutes, until everything is starting to brown.
While the vegetables are roasting, make the dressing. Add all the ingredients for the dressing to a bowl and whisk until smooth. If the dressing is still too thick, add a bit more water.
Add the greens to a bowl. Drizzle some dressing on the greens and toss to combine. Top the greens with the roasted carrots and squash. Top everything with the almonds, cranberries, and parmesan cheese.
Serve immediately and enjoy!