I have vein problems, so driving in a car that long is very painful - 2 hours in the plane is about all I can take anymore.
Anyway - I drove several times long ago, before the days of VCRs and DVDs for the car. My habit from NJ was the following...
We left after dinner. Last day of work, would sleep anyway if we left the following morning, but you get down past DC by midnight. Always have a triptick from
AAA and my state by state books, so I could find decent lodging and gas/food pretty easily - always look 60 miles a head.
Games - Count the neon south of the boarder signs the next day... If memory serves me right, there are 500 billboards.
State license game - try to collect as many different ones as possible (yes you can get all 51 - I have seen 3 hawaii's in the last 10 years. 50 states and DC. (give 5 points to the kid that figures out 51 possibilities)
Each out of state plate is worth 1 point.
If you call the state your currently in, you loose 1 point.
If it's a vanity plate, it's 2 points. (out of state and bonus)
If it's a Handicap plate its 2 points. (out of state and bonus)
If it's VW Beetle its 2 points...(out of state and bonus) with daisy hubs - another bonus...
So if your in North Carolina and a VW Beetle with handicap plates from NJ PLATE - BUGME2 and it has daisy hubcaps - you get 5 points for that car.
We usually limit it to max of 5 per state. Team with the most points gets to choose where we are having dinner.
Finally we would have a supply of cards, travel yahtzee, travel connect four, and fun topics with us.