How to Plan Meaningful Road Trips

Road in Kenton Oklahoma

Our return from the Kentucky Political Science Association conference could have been an uneventful run back up I-69 to I-75 and home.

Instead, Dr. Spence took the back way, a trip through the Land Between the Lakes on a bridge over sunken towns. Instead of eating at a fast food joint, we stopped in Hopkinsville for dinner-plate-sized burgers at a diner that fit maybe eight people huddled together. We traded the miles and miles of concrete for scenes of Kentucky’s rolling hills.

After that trip, I longed for others like it. But there was a problem…

I had trouble deciding where to go. Sometimes I thought that if I just got in the car and started driving, spontaneity would take care of the rest. But more often than not I wound up going nowhere new.

I found that like anything else in life, taking a meaningful road trip requires a plan, however simple that plan might be. Over the past five years I’ve found a few ways to spark a road trip to remember, and I’d like to share them with you.

1. Travel with your reading

One of the more memorable trips that my wife and I took during our years in Oklahoma was a weekender to Kenton, Oklahoma. I had just finished reading Timothy Egan’s book The Worst Hard Time, a gripping account of the Dust Bowl. Many of the stories in his book took place in Boise City, near Kenton.

Framing your trip around the book you’ve read makes what might seem boring far more interesting. Instead of seeing a quaint courthouse in a desolate town, I saw a crowd of farmers erecting a noose to let other farmers know what it means to buy land that was re-possessed and auctioned.

With some imagination, visiting the places that you read about is a more fulfilling experience. This will also motivate you to read about the places near where you live.

2. Make lists of similar places that you want to go

I’d use the term “bucket list” but that implies that it’s a list of places you’ll never go unless you find out that you’re dying. What a downer. But the concept of making wish lists is helpful for planning road trips.

Some examples would be baseball stadiums, obscure museums, ghost towns or battlefields. You could visit breweries, hole-in-the-wall restaurants or historical landmarks. Roadtrippers has some excellent lists that might give you some inspiration.

Using lists helps because it involves setting a small goal. Making a list gives you motivation because you don’t want to quit on it. And it gives you something to look forward to, as well.

3. Plan short road trips with several stops nearby, not a long trip to one far-off destination.

This is useful for a couple of reasons. First, taking shorter trips is cheaper. I’ve found that even when you try to be frugal, you wind up spending more on long trips than you thought that you would.

Second, usually when you set a far-off destination, you usually forget to enjoy the trip. In my experience when you make the trip itself a painful burden, it takes away from the destination once you’ve gotten there.

I’ve found it helpful to pick a town or region and plan to visit two or three nearby sites. The variety will also help keep you interested when it comes to smaller, local sights.

4. Use Wikipedia to find local oddities near you

I’ve developed this habit of searching Wikipedia for information about towns whose names we see on the highway signs.

Sometimes you may not find anything of interest. But every town, however small, has a history and you may be surprised by what you find when you start asking more questions. I found, for example, that Zilwaukee was so named to confuse and thus attract German immigrant workers who were looking for work in Milwaukee.

What I love most about taking road trips is that there is always a story to be told. No matter how insignificant a place might seem, it could have a very fascinating history.

Lastly, don’t be afraid to talk to the locals.

The reason that the road trip is the way to see the real America is that it opens you up to the lives of Americans. It exposes you to history, culture and tall tales. Sometimes the destinations are

I hope that these ideas will help get you on the road. I’d love to read in the comments of any out-of-the way trips you’ve taken, or how you find meaning in the road trip.

Tell a friend!

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