My father and I drove through Maine in October, 1993.
If you enjoy brisk weather and fall foliage, next month would be a great time to visit.
The receptions we got when we were in Machias and Lubec were less than friendly. If they’re not part of your itinerary, then I’m sure the excellent suggestions posted above will more than compensate for not including them.
Just outside of Lubec, we saw a sign that read:
WELCOME TO LUBEC
EASTERNMOST TOWN IN THE US
SETTLED IN 1785…INCORPORATED IN 1811
▲ I’m not shouting, it’s just that the sign was all caps.
The northern apex of our trip took us to a hill overlooking Riviere-du-loup, Quebec.
From there we looked down and saw a magnificent view of the St. Lawrence River, which is about 10 miles wide and verdantly green at that point. :D
On our way back to Saratoga Springs, NY, we stopped in Bennington, VT and hit the Ben & Jerry’s there, where we received a much warmer welcome than we did in those other two places.