The Two Secrets to Planning Your Next Great Road Trip Adventure

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Sunset over the Mississippi River in Vicksburg. All photos CC-BY-SA Ruth Suehle

The secret to a great summer is a great road trip, and the secret to a great summer road trip is so simple, it can be summarized in two steps:

First, plan.
Then get lost.

My family is road trip people—both the family in which I was the child and the family in which I’m the mom. I’d been 1,200 miles from home but never gotten on a plane until college, and my husband and I have been road-tripping together practically since we met. The first was fairly early in our relationship, from South Carolina to Philadelphia in his 1993 Ford Ranger. My mother remarked afterwards that if you can stand to be in the cab of a pickup with someone for that long, the relationship will probably work out.

Somewhere along the way, the trips started getting names, starting with The Great Western Adventure (part 1, then we flew north for part 2), and going on to include The Great Northern Baby Adventure, The Great Germany-Italy Adventure (we cheated and took the train from Munich to Venice), and The Final (Countdown) Shuttle Launch Adventure. Those links will take you to Google Maps for each path—I recommend any of them for a shortcut to your own Great [Fill in the Blank] Adventure.

Last summer we embarked on The Great No-Child Adventure of 2012. We planned it in just two weeks, which is practically spur-of-the-moment spontaneity when you have two kids under six. It helps that we left them at home, as the name implies. But the two-step plan still applies even when you bring them along.

Step 1: Plan

What I mean by “plan” is really “create serendipity.” Don’t sit back and wait for magic. Bring the magic to you, and put yourself in a place for the great happy accidents to happen. We could have just launched off for New Orleans, Memphis, and points in-between (which was roughly the plan), but without a little Google-assisted planning in advance, I’d never have known about Birthplace of the Frog, the Jim Henson’s Delta Boyhood Exhibit. And without that discovery, the docent there never would have sent us to Connie’s Kitchen, which may not look like much, but certainly will always be remembered as some of the best road trip food we have ever, ever eaten. (They put sugar in the collard greens. This is genius.)

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Of course, you should feel free to plan your stops around interesting filming locations. This is Longwood Plantation/Nutt’s Folly, aka the home of Russell Edgington, former Vampire King of Mississippi.

My two favorite sites for planning such adventures are WikiTravel and Roadside America.

WikiTravel tells me the basics. Am I going to hate having a car in that city? What are the must-sees on every tourist’s list? I generally browse the restaurant listings there, and they tell me one very important thing. If the list has only five restaurants, and two of them are Ruby Tuesday’s and Subway, I should find another town to eat in. Sometimes, though, they suggest a gem that I don’t find on any other list.

With all that need-to-know out of the way, Roadside America is where the real created-serendipity happens. Frommer’s and Lonely Planet won’t tell you where to find the Sacred Shrine to Bon Jovi, Cookie Jar Heaven, or a shell-shaped Shell station. The best thing we wandered into on last summer’s trip was The Minister’s Tree House, which is the sort of edifice that simply defies explanation. No photos could do it justice—nor describe the special feeling (I believe it’s called “Warning! Imminent injury likely! Possibly death!”) of climbing to the top of a massive piece of construction that’s never met a single building code. Or architect. Or in some sections, plain common sense.

Combine these two by using the “My Maps” function in Google Maps to start creating your road trip map. Lay down points for the odd things you find in Roadside America, places your friends have recommended, places you want to eat—anything that’s important to you. Color code them so that they’re easy to recognize when it’s 9 p.m. in the backwoods of the Mississippi Delta, and you’re trying to figure out where to stop for the night. If you look at the map I created for The Great No-Child Adventure of 2012, you’ll notice the color-coding starts to fall apart. Those are the items I added from my phone while on the road. It’s never too late to plan a little more serendipity!

Step 2: Get lost

Once you’ve planned for your serendipity, it’s time to get off the path and get lost. Find the most interesting road that intersects as many of the points on your map as possible. Hint: it’s not the interstate. Sure, there’s a chance that you’ll try to find a park you had on your map, miss the turn, take a bridge, and end up accidentally in Arkansas—a state that wasn’t even on your road trip plan—in the middle of a farmer’s field looking back at Memphis, where you intended to be. But that’s what road trips are about. Take a picture and figure out how to get back on track.

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These examples aren’t examples. They’re stories. And stories are the best souvenirs of a road trip.

And of course, just because it’s not on your map doesn’t mean it’s not in the plan. You might find an interesting brochure at a road stop or have a conversation in a McDonald’s with a stranger who recommends a devoted collector’s car museum you can get to. (Note that the very few reasons you should be in a fast food restaurant during your road trip include Ronald Reagan’s head and Sanders Cafe, a.k.a. the first KFC.)

Meet Rusty’s TV and Movie Car Museum. They’re not all originals, but they are all fun!

Most importantly: Avoid having a plan you can’t change. Stop worrying. And bring back stories.

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By day, Ruth works to make open source software communities better. The rest of the time, she makes things, which means her husband and kids know to watch out for stray sewing pins and to ask before eating anything made of fondant.