yup, the new road looks much better.

As for the scale, I wasn't asking for exact measurements, just a general idea like half mile long or 100 miles wide, that sort of thing. A small valley that can house and feed a decent sized city is good enough Given that, a few suggestions; Bring the mountains right up to the Towers of the Mountain Gate, and make the Mountain Pass a bit narrower. Possibly bring the south branch of the river out through the Gate as well in order to give the impression that the valley is higher than the path up to it.

Remember, these are only suggestions and I will not be heart broken if they do not fit what you need. This is your map and your vision so go with what you feel is right. You definitely have a vision in your head, so run with it You are doing good so far