Question

Like start at c:\ (or whatever the main drive is) and then randomly take routes? Not even sure how to do that.

public sealed static class FolderHelper
{
    public static string GetRandomFolder()
    {
        // do work
    }
}

Answer 1

Try getting a list of all the folders in the directory, then generate a random number up to the number of folders, then choose the folder that relates to your random number.

System.IO.DirectoryInfo[] subDirs;
System.IO.DirectoryInfo root;
// assign the value of your root here
subDirs = root.GetDirectories();
Random random = new Random();
int directory = random.Next(subDirs.Length);
System.IO.DirectoryInfo randomDirectory = subDirs[directory];