Hi All. Just hopped on board CartoTalk!
Ryan, I agree with the observations from Dennis. Visually I prefer the state boundaries from your first rendition posted over the line with a dash over top. Particularly as it appears over Lake Champlain. Perhaps the gray line underneath the lighter dash could be the color of a single dashed line for the boundaries. It seems that the color would still hold up over the green terrain. Also, I would recommend making "Green Mountains" more visible, part of the lettering gets a little lost (maybe making the color just a bit darker)--and I agree with the caps for "Long Trail" and "Green Mountains."
As for the townships, all of the location labels outside of Vermont, in NY, NH, and MA could possibly be smaller. I find my eyes moving to the left and right to read the town names (especially because their dot points, as Dennis pointed out, are highlighted with the light colored ring). I do not sense their significance for emphasizing the Long Trail. In fact, for hikers, towns closer to the trail would be more useful to know about. However, I do not think you need to add any more town names unless they are a very small font. I do think the map looks much better with the dull color for highways when compared with the first map you posted.
As a Vermont native, I think you have displayed it quite nicely. I have given a ride to LT hikers coming through town, so it brings back some good memories ... very friendly folks
I hope you are having a beautiful autumn!