I’m not sure why you want to clip their wings, most of us find it unnecessary, but here is a link to an article in the learning center above on how to clip.
https://www.backyardchickens.com/a/how-to-clip-trim-the-wings-of-your-chicken-to-prevent-flight
With living animals you don’t get 100% guarantees. That’s just the way it works. No matter what anyone says someone else can always find an exception. But there are some things that are pretty close to 100%.
It is pretty close to 100% that chickens do not know to stay off of roads. They certainly do not know to look both ways before crossing the road.
This does not mean your chickens will seek out the road to play in it. Many people free range chickens around roads without a problem. The risk is always there but whether or not they use the road depends on your flock and your terrain. Some flocks roam a lot further than others. How far the road is from the coop plays a part. Your terrain makes a difference. Do you have a barrier between the coop and road? That might be an area you don’t mow, a fence of some type, or a row of bushes. The only way to determine how big a risk a road is for you and your unique situation will be to try it.
Aart’s suggestion to let them out near sunset is a good one. Initially they won’t wander far from the coop, but as they get more comfortable they will range further. You’ll need to observe and see what you are comfortable with.
Something that is really close to 100% is that once chickens are used to spending the night in the coop they will return to that area at night to sleep. Usually that is inside the coop but occasionally it will be next to the coop. It’s usually pretty easy to catch them after dark and put them in the coop. Hopefully the area is not brightly lit. After doing this a few times they should get the message and start going in on their own. I’d give them at least a week of being locked in the coop or coop and run before I tested this, with two weeks being even better. If you do have a run, wait until they are going from the run to the coop at night before you let them out.
It is really hard to herd chickens anywhere. If you try to herd them they tend to dart out to the side. It can be really frustrating. That’s another reason why letting them out an hour or so before dark is a good idea, at least to start and you gain some confidence. But a good trick to know is to teach them to come to you. Put a treat they really like, maybe scratch but it can be something else, in a container (a bucket maybe) that rattles when you shake it. A couple of times a day feed them treats while rattling that can or maybe chanting something like “here chicky chick”. It should not take long for them to come running to you whenever they see that container, here the rattle, or hear your chant. That can be very useful to get them back into the coop or run during the day. Just be consistent and always give them a treat when you call them.
Getting them back in a t night really should not be a problem, they should want to go back in by themselves. It’s getting them back in during the day that can be the problem. I suggest you ease into it, more for your self-confidence than anything else. Easing into it should lessen you stress level.
Good luck!
