North Dakota's Theodore Roosevelt National Park

The best trips are littered with mistakes, frustration, and, if a river called the "Little Misery" runs through it, boot-sucking mud.

Heading out the door? Read this article on the new Outside+ app available now on iOS devices for members! Download the app.

We were in Theodore Roosevelt National Park, on the Achenbach Trail. Jeff and I had journeyed to the North Dakota park for the grasslands, badlands, buffalo, and prairie dogs. Autumn was in the air and all was pleasing to both eye and soul-until we hit the Little Missouri River. Pioneers dubbed it the “Little Misery” for its ability to inflict hardship: It can run so dry in summer that the ducks forget how to swim, or, following a storm, it can wash away all in its path.

Where we crossed, the river was slow as molasses and dark as chocolate milk. For some inconceivable reason, I waded right in, boots and all. Four steps later, the metaphorical tide turned, and the river’s nickname hung over the rest of the trip like a dark, swollen rain cloud. I sank in mud akin to quicksand-“pudding hiking,” Jeff called it-and ruined my new boots.

That night, we camped atop a grassy butte with the stars in easy reach. Just before dawn, an earth-rumbler of a storm broke, and fingers of lightning clawed at us as we ran like fools. In the confusion, I lost an arrowhead neckpiece, a keepsake from my grandfather, a man who shaped my life in quiet ways. It was powerful personal medicine, and it was gone.

We hiked the Buckhorn Trail the next day, having been assured by a ranger that plenty of water awaited in streams. There was dust in our water bottles when we met a British couple coming out. No water, they said. We crunched on food that needed water, spent a restless night, then made our parched way out the next morning.

After filling up, we decided to hike to the Elkhorn Ranch site, where President Roosevelt had homesteaded. We parked on public land, next to a bullet-riddled car bearing a sign suggesting that visitors go elsewhere. As we hiked, I listened nervously for small-arms fire in the distance and kept a wary eye on the undergrowth.

On the final day, the undercurrent of discontent that had rippled through the week smothered me, and I felt like a 4-ton toad was sitting on my chest. We hadn’t encountered catastrophes of biblical proportions, but all the little mishaps had ganged up and stained my mood. That’s not the way to end a trip.

But today, as I look back, it was one of the best trips ever.

Experiences that are effortless and instantly glorious are also superficial. They smack you between the eyes, then swiftly fade into distant recollections. You need snapshots to remember those trips.

The “best” sneak up on you down the line, settling in slowly and evolving into priceless lessons learned. Some of those lessons border on the painfully obvious, the tangible: You study the map pretrip and plan for obstacles, like rivers. You never pitch your tent where you’ll be a lightning rod. You raise a quizzical eyebrow when someone insists there’s plenty of drinking water.

Other lessons are intangible but pivotal, such as learning the difference between friends and acquaintances. The latter are people with whom you spend time, but share no meaningful bond or deep thoughts. Those relationships are like wood, easily splintered. There’s iron in true friendship, though, and with those people, you share lives and lifeways. There’s a link solidly based on a mutual passion for-and experiences that occur in-the outdoors, where the intensity of reward and failure doesn’t take pity on fair-weather relationships.

You also learn that a lost can become a found. I came to realize it was best-appropriate, even-that my arrowhead stayed in the Northern Plains. Better there, the homeland of great native nations, than on some East Coast sidewalk. My grandfather would have preferred it that way (and, no doubt, chuckled over my lightning two-step with his inevitable question, “Now what did you learn?”). He was fascinated by Native American ways, and with that fascination came deep respect. That lost piece of knapped chert was a seed planted in the High Plains that sprouted into a spiritual link between me and him and land he would have loved. My lifepath now winds through the North Dakota badlands and, someday, I’ll retrace it.

You learn, too, about the power of wilderness and how it’s sometimes best to go it alone. Before Jeff arrived, I spent 3 restless days wrestling with personal demons. On the third day, I found the mirror in the wilderness; I realized that raw, untamed land is the best reflector of a person’s strengths and character, but also of his weaknesses, flaws, and insecurities. Spend enough time Out There alone and you’ll see things about yourself that you can hide while in a crowd or with a hiking partner.

When Jeff arrived, I was staring wide-eyed into that mirror and unhappy with what I saw. But like the prairie dogs, my demons hid deep when they saw someone coming, leaving me even more emotionally contorted. That was the root of friction that smoldered between Jeff and me throughout the trip. He had stepped unexpectedly into my messy personal quest for answers. He gave me the space I needed, though, and as a result, the answers eventually came to me, like iron filings to a magnet. And a strong friendship was forged, as well.

What makes the “best” trip? It’s not the landscape, not the critters, or the sunset. It’s what the experience does to you, for you.