I grew up just outside of Plymouth, Mass and had grandparents living in the Berkshires of Mass. I now live in Maine.
What I would do is as follows:
Stay away from New York City. There is never a way to know if there will be nasty traffic or not. Plus a little to the West and the sites in Pennsylvania and New York are a lot better.
I would try to stay in Pennsylvania, New York hotels will likely be more expensive.
From New York try to head towards Pittsfield, Mass. It is not a great destination, but will lead you to Route 7 up into Vermont. It is a great drive and one used for leaf peepers. In Vermont you will arrive in Bennington which is a fun “artsy” town to look around.
After Bennington, set your Navigation to Bethel, Maine. You should be taken through some great small and rural towns through Vermont and New Hampshire. Plenty of small towns to visit and a really pretty drive. You will probably drive right through White Mountain national forest.
Bethel Maine is not far over the border into Maine and is known for Sugarloaf Ski Resort and sits in the middle of a great place to look at fall foliage.
Much depends on the time of year, but this route should provide a really easygoing and pleasant bit of sightseeing.
If you get near Adams, Mass I can really strongly suggest a lunch at Angelina’s subs. Remember to ask for the Dust! In Bethel try something Laos from Le Mu.
Adding to the list. Thank you.