We are in CT and have taken plenty of road trips throughout NE. Each state has their own jewels to see, but it really depends on what your interests are. Unless, I missed it, I didn’t see a time frame for you trip either. There are a lot of good suggestions here, but from Upstate NY, to Arcadia NP in ME to The Cape in MA will take some time.
Late September/Early Oct would be a good time for a road trip. IMO, just the natural beauty is the biggest draw when driving through NE.
A ride up RT100 in northern VT is great. There is the Cold Hollow Cider Mill, Cabots Cheese & Ben & Jerry’s factory all very close to the beautiful town of Stowe. If anyone bakes, then a stop to King Arthur Flour in White River Junction is a must do.
In NH, the White mountains are beautiful anytime of the year and you have to take RT 112, the Kancamagus HWY is a National Scenic Byway.
ME is a bigger state than most people think. If you have the time, a trip to Arcadia NP is well worth it. In Freeport, there are lots of shopping Outlets, but most notable is the huge LLBean store, open 24 hours. Kennebunkport is a great town to explore and home to Walkers Point, the Maine home of the former President Bush. While you can’t go up to the house,(really group of houses) it’s on a peninsula with a guard house, there is a turnoff where you can park and get out to look at it.
If you can make it down to MA, the coastal road along NH to MA is a great ride with some beautiful houses. Swing up north of Boston to Rockport and Gloucester, where the movie “The Perfect Storm” was based on and filmed. Boston is rich in history, but driving is a bit crazy. If there is time to keep heading south, there is Plymouth, (something about pilgrims) and on to “The Cape” as we like to call.
On your way way back, if you can stop off at Newport, RI to see the “summer cottages”, you won’t be disappointed. I would recommend that for anyone.
If you have any specific questions, I would be glad to help if I can. Happy Planning