Illustration: Kevin Howdeshell / kevincredible.com

Denver has always struggled just a little bit to define itself, wavering like the weather between being a cowboy kingdom, a pioneer paradise, some sort of alpine L.A., a mellower Boston or an open-minded Arizona with better sports teams and real snow. For me, Colorado has always been that place where people from everywhere else come to findthemselves.

It’s one of the great crossroads along America’s migratory route where approaching highway travelers can watch those mountains getting bigger by the mile, growing with that impending sense of transformation that you are somewhere between who you were and who you are.

Which is why I was so glad to read in the Denver Post that East High School, the pinnacle of public education in this town, which for decades has served as a never-ending melting pot of poets and punkers and politician’s kids, was going to give an honorary diploma to Neal Cassady. It was Cassady who Allen Ginsberg described as “the cocksman and Adonis of Denver,” and who serves as both the wildhearted playboy opportunist and eternal itinerant trickster of Beat Generation yore.

Of course, I was excited because I went to East myself, and still get nostalgic about all the days I spent looking out those classroom windows dreaming of all the places I would go and places I would leave. But also because as the character Dean Moriarty, it is Cassady who drives the narrative of Jack Kerouac’s iconic “let’s get in the car book,” On The Road. Cassady who pulses with all that disparate energy, ennui and immutable essence of time suddenly leaping away whenever you spend more than a second standing still.

It is Cassady who asks Salvatore “Sal” Paradise, the Benzedrine-addled narrator of On The Road, “What’s your road, man— holyboy road, madman road, rainbow road, guppy road, any road. It’s an anywhere road for anybody anyhow.”

And it is Cassady who epitomizes why Denver is the road-trip capital of the world.

Four Strong Winds

For Kerouac for sure, there are few—if any—other places in this country where the simple act of choosing to head North, East, South or West can summon such various visions of either snowfields, glaciers and grizzlies, or factories, cornfields and freshwater, or Southern belles, sandstone and Sonora, or that forever feeling of traversing first the mountains, then rolling down the long fall out to California, to the endless ocean and nothing more.

“As we crossed the Colorado-Utah border I saw God in the sky in the form of huge gold sunburning clouds above the desert that seemed to point a finger at me and say, “Pass here and go on, you’re on the road to heaven,” Kerouac wrote.

In the book, and in the urban reality of commuting these city streets, in search of a good slice of pizza or homegrown local pub, it’s as if Colfax Avenue provided some metaphorical meridian for the U.S., pointing to Manhattan in one direction and Hollywood in the other. Lined as it is with greasy burger joints, barred window liquor stores, hookers and hash houses (and even the capitol building itself between all the neon-lit possibilities for porn or prayer), for anyone taking the long look left or right, you can see the people getting progressively whiter as you head for Canada, or darker if you follow the southern stars down to Mexico.

You can see how just by turning down one street, or going one stoplight further, you might eventually find yourself out past the city, with speed limits lifting and the wind in your hair. You will be ready, as you are, to see something that you’ve never seen before.

Now

The secret, of course, is in giving yourself the freedom to go. For Kerouac and Cassady, and Lewis and Clark, and Ponce de freaking Leon, it was so much easier without the internet and the cellphones and unread books on Nook and must-watch cable shows to get just a few hundred yards from the last town on the map before they really were on their own. But the search was the same, to be out under the naked sky, crazy in love with the entire world and all its universal subplots and epiphany-inducing shooting stars, trying to embrace all that youthful possibility you feel.

“My witness is the empty sky,” Kerouac said, as if all that unfettered nighttime beauty was waiting for him alone.

It’s certainly waiting for you. And not because it needs you, but because it wants to remind you of all the bigger ideas you used to have the heart to hold. It wants to remind you of what it feels like to be in motion, not worrying about what the neighbors think, or that there is even a neighborhood at all.

“These roads don’t move, you’re the one that moves,” alt-rockers Ben Gibbard and Jay Farrar sing on One Fast Move Or I’m Gone, their tribute album to one of Kerouac’s other books, Big Sur.

That observation is just as applicable here. And so is the idea that it’s just as important that you don’t waste another weekend or week of vacation or even an afternoon sitting around your living room waiting for one same-old fun night on the town. Because it will never surprise you or satisfy you, or give you that warm, deep feeling that only true experience will ever give you.

So go. All of this will always be waiting for you if you want it to. This town has spent so many years acting as a beacon before, burning for every bright-eyed moth searching for something more than Oklahoma or Omaha could ever offer.

Out there on that very road, imagining his own return, Kerouac wrote, “I pictured myself in a Denver bar that night, with all the gang, and in their eyes I would be strange and ragged and like the Prophet who has walked across the land to bring the dark Word, and the only Word I had was ‘Wow!’

Peter Kray is Elevation Outdoors’ editor-at-large  and co-founder of The Gear Institute (gearinstitute.com).