Oh man, planning a fun road trip is key! For a drive from NYC up to Boston, definitely consider taking the coastal route through Rhode Island for a bit. It adds a little time but the views are worth it. I found this awesome article with a bunch of hidden gems and diner recommendations along that general corridor. Check it out on this site
https://buffalonews.com/exclusive/article_86aa387a-e106-55d0-a980-0b0a1b50db05.html .