I would come up through the Adirondacks and cross into northern VT, then head south east towards NH by way of VT 108, aka Smugglers Notch. I would suggest planning it so you can stop in Jeffersonvulle and have a meal at The Family Table, right on 15, a friend of mine owns it and its a fantastic restaurant, closed Tues and Weds. Into NH plan on hitting the Kancamagus RT 112 from the Conway area over to Lincoln, it runs right through the White Mtns and is a real nice road. Cross into Maine around Fryeburg and right through maine's western mtns, watch out for moose through VT, NH and ME. Maine is a big state with a whole lot of nothing, its worth it to go up to Baxter State Park, but way north of where you will be, if you like the coast you may want to head towards Bar Harbor and work your way down Rt 1, I would stop in Portland if you like cities. In MA it really depends what you want, we have rural mountainous areas, but they are west and can't compete with NH, ME and VT so you may want to switch to urban mode and hit Boston, maybe check out the Cape if you're into that. Central MA is more for residents than tourists, there are cool spots, maybe because I live here I discount what's close, I don't see many tourists around here though. I would also skip CT, maybe hit RI instead. Providence can be a fun city and there are fantastic restaurants, hosting Johnson and Wales leaves plenty of aspiring chefs who work cheap, you could also hit Newport. Enjoy New England, having lived here my whole life I can say it s a great place, you'll see lot's of cool sites and meet some nice people. Keep in mind you will find people very different state to state, more patient and friendly up north, more hustle and bustle down south.

And as an example 108 doesn't go all the way to NH, just saying you should plan to hit it, you will have to plan out the trip and just include the roads I mentioned if interested.