Nice pictures; looks like a nice day. Our family has spent about four summers in Rockport so it was nice to see the sites again. I really enjoy riding Cape Ann, but I refrained from answering your question because I didn't know what kind of rider you are. I commute in Boston so rockport was great. The other posters gave pretty good opinions, and narrow roads could be trying if you're not used to them. I don't remember a lot of potholes though.