I echo a few others in the forum: What are you wanting out of the trip? Simplicity? "Easy" driving (Yeah, RIGHT!)? Lack of tolls? It's up to you to decide.
That said, from Port C. I'd take 75 to Atlanta, around the EAST side (less traffic) on 285 to 85 North. Then, 85 to 77 in Charlotte, 77 to 81 in Virginia. Then — and this is the good part — you get to traverse 81 all the way to Scranton, drop south a few miles to pick up 84 and track that all the way to the Mass Parkway and 290 into Littleton. You cross the Hudson at Newberg, NY — WELL north of the Big Apple! — and you're home free!
I choose this route because I used to live in Roanoke, VA, and 81 is, to me, one of the most beautiful drives of Interstate there is! While there can be accidents and backups anywhere, along ANY (well-planned?) route, the I-95 and that nightmare known as The Capitol Beltway as well as getting through Baltimore and points north just aren't worth it! I ran your itinerary through Google Maps and the I-95 route takes 21 hours and 48 minutes... I-81 via Scranton: 24 hours.
Not having a KILLER headache when you arrive: Priceless.