So it looks like we're headed South through Chicago and then East to Brooksville (Maine) in a few weeks. Originally we were going to stop in Hartford one night along the way, but our potential hosts are previously booked. So now we can basically pick any route we want, and sightsee along the way as we deem it appropriate.
One thought was to go through Montreal - - I used to love that city and it would be wonderful to see it again. But I haven't tried to cross the Canadian border in a long time and I thing I heard it's gotten to be a pain.
So, assuming (1) a limited budget; (2) a canine companion; and (3) a reasonably flexible schedule, what routes do you suggest and what should we stop to see along the way?