Columns > Published on July 17th, 2018

7 Tips For Your Summer Road Trip From Jack Kerouac

Images by Ben C.

On July 17th, 1947, Jack Kerouac went on his first cross-country road trip — a trip which would inspire him to start the book, On The Road.

Since then, Kerouac’s magnum opus and beatnik odyssey has done more than just influence a generation of readers and writers: it’s also motivated people to travel.

To help all the Kerouac fans who are planning to finish up the summer with a road trip, we’ve compiled seven On The Road-inspired tips for you to bring along.

1) Just do it

There was nothing to talk about anymore. The only thing to do was go.

A road trip is a big undertaking, and it’s easy to get trapped in the neverending planning and research phase. But at some point, you have to make the decision that you’ve prepared as much as you can and the only thing left is just to go.

Kerouac himself was all about less talk and more action, exemplified by one of his most repeated quotes:

Because in the end, you won’t remember the time you spent working in the office or mowing your lawn. Climb that goddamn mountain.

2) Remember to appreciate the journey

They have worries, they're counting the miles, they're thinking about where to sleep tonight, how much money for gas, the weather, how they'll get there — and all the time they'll get there anyway, you see.

Think back to the feeling you had when you put the keys in the ignition of your very first car. Remember the sudden freedom you experienced as the engine roared to life? That’s what road trips are all about: the freedom to explore. Of course, spotting one of your destinations on the horizon is an exciting feeling, but Kerouac would remind you to enjoy the twists and turns on the way. When you’ve got somewhere to go, a flat tire won’t throw you off your course.

That being said, maybe...

3) Plan, at least a little

There was nowhere to go but everywhere.

This is one instance where we’re going to play devil’s advocate to Kerouac. We’re not saying you have to totally nail down your itinerary (unless that’s your thing!), but even Kerouac had a general destination in mind: West.

The truth is, unless you have absolutely unlimited time to wander wherever the wind blows, you can’t see everything or go everywhere. And as fulfilling as it is to stumble upon beautiful places or experiences, it’s also incredibly rewarding to put work into arriving somewhere you always wanted to go.

4) Pause for sunsets

Soon it got dusk, a grapy dusk, a purple dusk over tangerine groves and long melon fields; the sun the color of pressed grapes, slashed with burgandy red, the fields the color of love and Spanish mysteries.

I know everyone talks about driving off into the sunset, but when you see the kind of sunset that Kerouac describes above, our suggestion is to stop chasing it and let it pour over you.

In fact, Kerouac had a big soft spot for sunsets, writing in his 1960 novel Lonesome Traveller:

Sixty three sunsets I saw revolve on that perpendicular hill – mad raging sunsets pouring in sea foams of cloud through unimaginable crags like the crags you grayly drew in pencil as a child, with every rose-tint of hope beyond, making you feel just like them, brilliant and bleak beyond words.

But this is more than just a poetic tip, it’s a practical one too: if you start your day on the road earlier, you’re more likely to stop earlier as well and beat traffic.

5) Notice the beauty in the mundane

His friends said, "Why do you have that ugly thing hanging there?" and Bull said, "I like it because it's ugly." All his life was in that line.

Chances are you’ll see a lot of highways and uninteresting landscapes on a road trip. When you do pass through towns, a lot of them will likely be small rest stops rather than places you’ve starred on your map.

But if you’re willing to stop and look around, you’ll see and learn so much by just witnessing the everyday lives of other people. After all, one of Kerouac’s big goals for his travels was just to "...go and find out what everybody was doing all over the country."

So if you find yourself on a stretch that feels “boring,” take a moment to figure out what makes that specific place tick, and learn to spot the beauty in that.

6) Keep a journal

Man, wow, there's so many things to do, so many things to write! How to even begin to get it all down and without modified restraints and all hung-up on like literary inhibitions and grammatical fears...

… Or if writing is not really your thing, find another way to meaningfully document your trip. The great thing about keeping a journal, however, is that it allows you to reflect after the fact. While grabbing a camera every time you witness something special can separate you from the moment at hand, a journal requires you to think back and remember what stood out about that moment.

7) Make your own list of road trip tips

The best teacher is experience and not through someone's distorted point of view.

While I’ve done my best to pour through the pages of On The Road to bring you a list of Kerouac-inspired road trip tips, the greatest way to learn how road-tripping works for you is to do it. Don’t take my word for it — maybe what worked for Kerouac won’t be your cup of tea.

But then again, if I’m telling you to take this list with a grain of salt, it means you can also throw Tip #7 out the window and follow this list to a tee. The path you take is up to you!

So go on, grab your car keys, pick up a pen, and write your own story on the road.

About the author

Emmanuel Nataf is a Founder at Reedsy, a marketplace and set of tools that allows authors and publishers to find top editorial, design and marketing talent. Over 3,000 books have been published using Reedsy's services.

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