We have a long drive too and a busy road at the end, all my dogs excluding our puppy mill mama, can actually be outside unattended and stay in their area even without a fence (I don't do that but it's happened before when they escaped) I do have them with me when doing chores outside often. When I take them for long walks we have to go down the driveway and across the road. One thing that always worked for us was to pick a marker we didn't want the dog to pass (ours is a tree halfway to the road) one person holds the puppy and then I scold the heck out of the tree, not the dog, expressing my disgust and hatred for the bad tree. I make the tree a horrible place for me to be and my dogs learned to hate it too, lol. I also praised the pup when he avoided the tree or looked at it and turned away. My dogs are trained well when it comes to leash work. They go anywhere if lead so they don't pass the tree on their own but with a leash they understand I'm leading them and trust that it's ok to pass if the leash is on and I tell them to.