We drove from Florida to Chicago back in the dark ages. We had a blast!
We drove at night the first leg of the trip to get to Illinois so they would fall asleeep in their car seats soon after it got dark. On the way home we usually drove during the day and we would have a blast. There is so much to see out the windows! Our youngest even surprised us on a later trip by asking if we were to a certain water tower he had noticed when he was 2 or 3.
We packed age appropriate things for the kids to do while they were awake.
Books, coloring books and colors, markers, sticker books, little cars, stuff for babies. Sometimes I sat in the back seat with them to help them or read to them. We bought the travel games like tic tac toe, , I spy, etc. where you just moved the sliding piece over the pictures and played those together, too. We counted cars. Once even did a vehicle study to see the number of vans passing us on the other lanes compared to the number of cars being driven.
We sang songs, we talked about school, family, and friends. By the time they were four we were doing the I spy a_____ games, the find the alphabet in order on the billboards and signs, the find the tags from every state games, and when the youngest was in kindergarten we made up an in the car jeopardy game that we had a blast with. One of us got to be Alec Trebeck, the other 3 were the contestants. Alec of course manned the answers and even our kindergartner was able to be Alec and think up words for us to find the question to.. He came up with things he knew from kindergarten, books, and tv. The kids loved stumping us. They also loved making the sound to answer. We would play and laugh for ours. Heading to Disney, thinking of Disney answers would be a way to keep them interested. Driving for hours was a way for a busy family where both parents worked,the kids were in school, clubs, and on sports teams to spend quality time together. Having 3 rows of seats also helped the situation. One sat in the middle row and one in the back so the seat next to them could be folded and work as a table for them.
We also did the gift at each state line to give them something new to look at or do. When they got older(both in school) we gave each one a roll of quarters. Told them that it was theirs to spend when we got there. BUT...... if they started picking on each other, the one who started it had to give me a quarter for me to spend on myself! Sometimes they both had to pay. LOL But it usually ended quickly if I took the quarters. The guys are 25 and 30 and we still talk about all the fun we used to have on road trips. My youngest is making one this month to DC for the inauguration and I just bet he will be having the 3 girls he is traveling with playing some of the same games we used to play back in the day .