Road Trip Gone Right: A Guide for Small Highways & Big Discoveries

A back road somewhere. (Photo by Martin Kallur,

The road trip is a time-honored setup for any number of American movies—Thelma and Louise, the National Lampoon Vacation series, and Into the Wild, to mention a few. While most of these films involve death or mayhem, fortunately my own road trips have not, so far, been that dramatic. For years I’ve been going on road trips every summer, usually with one of my kids. Some summers it’s been just a long weekend or two camping around the state. Other times, it’s been weeks out of state or even out of the country. If you are considering a road trip—and I heartily recommend it—here are a few suggestions for a successful trip.

What to Bring

The most important thing to bring along on a road trip is a good attitude. Things can go wrong. Correction: Things will go wrong. Count on it. I’ve lost my wallet with all my credit cards in Tokyo. I’ve had to sleep overnight on the marble floor of an airport. I’ve left the tent poles home during a camping trip. I’ve been hopelessly lost. Hmmm, maybe I’m the problem here . . .

In any case, your attitude will make a big difference. Being lost can be a fun adventure or an anxiety-filled exercise in frustration. Forgetting to bring the tent poles can make for a miserable trip or be a test of your resourcefulness.

The next thing is to bring on your road trip is a good companion. Sure, you can go on a solo road trip, and I’ve done a few. The charm in that scenario is that you can eat where you want, stay where you want, and travel as long as you wish. I once spent an entire afternoon checking out the wonderful and varied architecture of a neighborhood in Mason City, Iowa. This was something that no one else in my family would have had much interest in. It is undeniable, though, that solo trips can also be lonely and dispiriting at times.

For me, the best road trips involve a single companion. Including more people than that involves too many compromises and endless debates. Of course, it needs to be the right companion. The ideal travel partner is adventurous, flexible, resourceful, a light packer, and, if not cheerful, at least tolerant of some adversity. Fortunately, both of my kids have these qualities. It was a revelation when I traveled with my son. Due to his autism issues, he can be extremely rigid in his habits and barely tolerates changes to his routine. But on the road, he doesn’t have a routine, so he is up for nearly anything.

Traveling with the right person can be an incredible bonding experience. You can learn a lot about someone by spending hours with them in a car. At home, my teenage son only speaks in monosyllables. On the road, he opened up and we talked for hours, sharing opinions on philosophy, music, politics, people, and society.

But even if you’re traveling with just one other person, some compromise is necessary. I’ve learned to put up with my son’s preference for headache-inducing music and my daughter’s habit of propping her bare feet on the dashboard, leaving footprints inside of the windshield.

Just remember, some people are not cut out for traveling. They don’t like surprises, prefer more detailed planning, and pack more for a weekend than I would for a month.

What Not to Bring

Actually, what not to bring on your road trip might be even more important than what to bring. I try to travel as light as possible. If I can’t carry it on my back, it stays home. If I need to check it in at the airport, I don’t bring it—and I get to skip the baggage carousel. If you discover you need something that you didn’t pack, you can usually find it elsewhere. I once went overseas for a month, forgetting to pack underwear. I now own unique and valued foreign underwear as souvenirs.

Richard Kurtz with his son Alex during a 2017 road trip in Japan and Korea

Getting to Your Destination

Road trips usually have a destination in mind, but ideally, it’s better to think of it as more of a target than a goal. A road trip should be about more than just getting somewhere. It should be a journey of discovery—discovery of the country, discovery of your companion, and possibly even self-discovery.

To discover the country, you need to leave the interstates behind and explore the two-lane blacktops and the small towns along the way. Stop at local non-chain gas stations and eat at mom-and-pop restaurants. Talk to the locals. What do they do there? Why do they live there? What do they recommend that you check out in the area? I have a friend who likes to go on mini road trips to visit small-town Iowa bars. We go for lunch and he chats up the locals. I’m way too much of an introvert for that, but I can appreciate his efforts.

Travel Journals

If you like to write at all, I recommend keeping a travel journal. Reading it later will remind you of the adventures you had and the sights you saw. You can experience it again where you otherwise might have forgotten much of the trip. I find that travel sharpens my senses and makes me more aware of my surroundings. Writing helps to capture those moments in my memory.

I’ve tried getting my kids to keep their own travel journals with limited success. Often the entries are along the lines of “We went somewhere and did stuff.”


This summer, I recommend you adopt an adventurous attitude, get a compatible partner, pack light, and go. And don’t forget to document your travels.