MA Route 2 is a wonderful drive, its unbelievably scenic on the western segment after the freeway part ends
Honestly if you want to see a more scenic and touristy part of NH, go to Hampton Beach or Seacoast. Nashua is pretty much plain suburbia, I only go there a lot since my best friends live up there.
New York State is not part of New England, nor is New York City or Long Island. Connecticut is kinda wierd, its like New Jersey in some aspects as its in the middle of two main cities despite having its own cities. Geographically yes its part of New England, but the southwest quadrant, West of I-91 and South of I-84 is very much NYC Suburbia so the culture in that aspect is very similar to places like Westchester or Long Island (tho Long Island is it's own animal altogether. Its a strange place compared to the rest of the country, and im sure the other islanders on this board will agree with me)
Now I dont know where you live but this route might be interesting.
from I-95 take the exit for Hutchison River Parkway, take that up to the state line where it becomes CT Route 15/Merrit Parkway. Its a lovely scenic highway. Its breathtaking in the fall when the leaves change. There is aalso a nice mountain tunnel further up. At Exit 68N-E take I-91 North towards Hartford. Stay on I-91 thru Hartford and North into Massachusetts. In Agwam MA there is Six Flags New England Im not sure exactly how to get there. Stay on I-91 to Exit 8 for I-291. If you value your life and safety DO NOT get off at any exits in Springfield, that city is one of the WORST in Massachusetts, crime and urban blight up the wazoo.
Take I-291 to the Mass Pike. Get off at Exit 15 for I-95/MA 128 and get off at Exit 32B Middlesex Turnpike, theres a nice Hilton Garden Inn there somewhere. I remember staying at it. Next day, Get back on 128 North to Route 114 in Peabody and head south into Salem MA. Salem is a lovely little city with lots of interesting magick related stuff. If you want to see boston, go out the way you came and take 128 south to US 1 south, youll see an intersting "Jersey Freeway" then the double decker Tobin Bridge into downtown boston. Go out via I-93 North into New Hampshire, Get off at NH 38 West and head on that till Pelham theres a lovely arcade called hte Pinball Wizard arcade full of old vintage arcade machines and skee ball and stuff. Head back on 38 to I-93 and go north on I-93 to NH 101, take NH 101 EAST across the state to the end into Hampton Beach, walk aroudn the boardwalk, enjoy the beach. head back on 101 to I-95 North and head into Maine, I dont know maine too well so youll have to do some research. Exit out of Maine on 95 South then keep going and take I-495 South, head on I-495 to Exit 29B MA 2 West and take Route 2 all the way across the state to Greenfield then take I-91 south back down to I-95 south, catch a glimpse of the reconstructed New Haven area then head home on I-95 south to whatever roads you take from the George Washington Bridge back to home (I have no idea where you live)