We drive from MA to Hilton Head, SC a couple times a year. 95 is obviously the shortest route but far from least stressful. On our way home this past April we got stuck in traffic before Richmond and decided to take "the road less traveled" and just work our way north. It worked out great and we saw some beautiful scenery in Va along the way.
Reversing the route would be some thing like this.
Take 84 to 684 to NY Thruway over the TappanZee Zee Bridge....follow 287 through NJ to Rt 78 towards Harrisburg, PA to Route 81 South. If you don't want to be on the truck route, when you reach Staunton, Va take Route 64 towards Richmond where you then link up with 95 which is clear sailing south of Richmond.
What we actually did was get off 81 in Winchester, Va and took Route 522 to Route 29 to 64 then on to Richmond. It was a beautiful ride through little towns and farmland and definitely stress free. Felt like a Sunday drive.
Another suggestion, would be to just leave CT at like 6:30am...go over TappanZee Zee to Garden State Parkway to NJ Turnpike to 95 all the way. Leaving at that time puts you in NY/NJ right at tail end of rush hour so you should be able to get through with minimal traffic and then be through Baltimore and Dc by 2:00... Just before afternoon rush hour. If you can get through Fredericksburg before 3:30 you should be ok after that. Up till that part, the ride is pretty stressful, however.
Also...if you decide to do the first route I mentioned, you can also just stay on 84 through PA and then connect with 81. When we did this one time, however, the ride seemed interminable. We definitely prefer going 78 through Harrisburg which cuts down on time....at least to us it felt like it did.
Hope this helps!!!