I did a very similar drive a few times going to university in Charleston, SC. I would usually stick 95 the whole way for time's sake, but if I were looking for something more scenic/less traffic and wanted two stops- here's my suggestion.
- Leave NH, head west to Albany through VT, then south to Warwick, NY and check out the winery.
- Staying west of NYC, head south through NJ, then go south through the DELMARVA peninsula and spend the night in Norfolk, VA.
- Head out of Norfolk and 7 hours later get down to HH.
Enjoy the drive!