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I drove from DC to Colorado (and back) recently. I stopped often to stretch and for potty breaks. But honestly, I pass the time by listening to the "noise" in my head. Therefore, I drive mostly in silence. Every once in a while I'd listen to a podcast. But mostly just me & my thoughts.
When I was married we passed the time by talking and playing music. I detest audio books. I can’t read in a moving car as it gives me a headache. Now alone I don’t take car trips because it’s too difficult having 2 dogs being alone. Plus I can’t drive long distances and everyone lives thousands of miles from me. With 2 people sharing the drive it was different.
I find looking out the window sufficient entertainment. That and a few snacks are all I need. Same for train rides. Sad that so many require so much other stimulation! I'd say most people just stare at their phones these days, or at least that's what I see happening in other cars when I look out the window or look at other passengers on trains. If I'm driving (in which case I can't really relax and take in the scenery), I like an audio book.
For any trip about 8 hours or less, we prefer to just drive, rather than deal with possible flight delays, lost luggage, needing a rental car etc.
We do the obvious things like audiobooks, listen to music, use books of conversation starter questions, even read interesting articles or jokes to each other. Are there other pleasant ways you pass the time on road trips?
Unless I’m traveling with my bike, I’m flying.
If I want entertainment let the radio scan for the next station. Like to get next town local broadcast, AM or FM. Like to see how far I can get listening to hometown station.
Had the 6 disc CD player in the trunk. Now the CD is replaced by a dongle.
It's just me, not we. If driving a car, I can drive for hours in silence and look at the world going by. Even in wide open barren landscape like you might see in the great plains in the US. Sometimes I'll scan the radio stations to see if something interesting pops up.
If I am taking a "road trip" via train here in Germany, it's easy. I have my Kindle book reader always loaded with a few new books, I'll relax and sometimes cat nap, or occasionally chat with another passenger on the train. I've met lots of interesting people of all ages on the train.
We drive from SoCal to our 2nd home in North Idaho every summer, 1300 miles. It usually takes us two to three overnight stays. We alternate between routes all depending on the weather, and we have CD collections that are selected to match the scenery, usually big movie themes for big Western landscapes. Driving through urban areas calls for classic rock 'n roll . I don't much like audiobooks on trips, because I find them distracting. We don't use Internet playlists, just our own collections. Of course we also talk, usually about upbeat subjects, planning our vacation, etc. Nobody needs their blood pressure going up while driving, it's stressful enough as it is!
We have to stop every 2-3 hours for the sake of our two dogs--and it's good for the circulation to get out and take a quick stroll and a stretch, anyway. Fortunately both dogs enjoy road trips; they are intensely interested in looking at the world passing by on the freeway. Even better if we drive more slowly through neighborhoods, with the windows down. And when they get bored, they curl up and go to sleep. I wish I knew how they process all the sights and smells. But they seem to remember special places from year to year, such as particularly nice rest stops with lots of grass. One year at a rest stop our dog Tribbles was apparently looking for a mouse she had seen there the previous year! At least we think that's what was going on in her brain. Or maybe she was following a trail created by generations of mice... Our dog Sweetie who passed away 9 years ago was the best road buddy in the world: patient, interested, happy to be with us, always ready for new adventures. Traveling with dogs can limit your options, but it can also be fun to be traveling as a multispecies family.
I simply enjoy the scenery. Even when there’s nothing dramatic I check out the vegetation on the side of the roads or how the crops are laid out.
Meanwhile I am attentive to all the traffic in front and behind, and tend to categorize driver behaviors in advance.
Then I stop for gas every time it drops to half a tank.
Can you tell I’ve made several 1000+ mile trips?
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. I don't much like audiobooks on trips, because I find them distracting. We don't use Internet playlists, just our own collections. Of course we also talk, usually about upbeat subjects, planning our vacation, etc. Nobody needs their blood pressure going up while driving, it's stressful enough as it is! 
