The Two Secrets To Planning Your Next Great Road Trip Adventure

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

1. Plan
2. 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. My husband and I have been road-tripping together practically since we met. The first was fairly early in our relationship and from South Carolina to Philadelphia in his 1993 Ford Ranger. I remember my mother saying if you can stand to be in the cab of a pickup with someone for that long, the relationship will probably work out.

After that, they 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 Shuttle Launch Adventure. I recommend all these paths to your own Great [Fill in the Blank] Adventure.

Most recently we embarked on The Great No-Child Adventure of 2012. We planned it in two weeks, which is practically spur-of-the-moment spontaneity when you have two little kids. It helps that we left them at home, as this trip’s name implies.

Step 1: Plan

What I mean by “plan” is “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, 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.)

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, and they often 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 list a gem that I don’t find on any other list.

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 or a shell-shaped Shell station. The best thing we wandered into on this 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 of a piece of construction that’s never met a building code.

Use 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

But 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 probably 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.

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 private 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, aka the first KFC.) Never have a plan you can’t get out of.

After years of doing it both ways, my recommendation for hotels is to book it on the road. The only hotel I booked before this summer’s road trip was one in New Orleans, which had two very appealing features: it was within walking distance from Bourbon Street and had free parking. Other than that, I used my phone to Priceline hotels. I sometimes consulted the Marriott and Hilton apps (hotels where I have reward points) and the Travelocity app, but Priceline was the winner for us almost every time. At around 8 or 9 each night, we’d see how far we’d gotten, decide where to stay for the night, and I’d get on the phone and find a hotel.

The implied corollary to step 2, of course, is “don’t be a priss.” The planned serendipity of flexible road tripping means your car will get dirty, and you could end up sleeping in a hotel with a cranky night auditor, hard mattress, and slightly peeling wallpaper. Let it go. If you need turndown service, four-star dining, and scheduled entertainment, road trip adventure is not for you. But if you’re willing to trade creature comforts for adventure, grab your keys, and let’s hit the road.

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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.