It hasn't happened lately, but in the past when I traveled further north I had to be very careful when near the Canadian border. If the signal jumped to a tower on the other side of the border (regardless that I was still on the US side) it could mean billing trouble. In my experience, if you can prove that you did not cross the border (produce a hotel bill, or a restaurant bill, or something that shows your physical location) the phone company will waive the roaming fee(s).
I've always purchased "national" plans, so I've never had to worry about state-to-state roaming or regional roaming.