you might want to clarify that you're leaving from kentucky. i know it's in your title, but i read your post as basically 'i am leaving from portland maine to new england' which confused me quite a bit at first.
as for advice, i'd just take the fastest route though those states up to the NE; you can hitch along the coast, but there's going to be more big cities and big highways there so while it's definitely not impossible, you'd probably have a better time of it going the more direct route than up the coast.