In May of 2011, Rinker Buck, his brother Nick, and Nick’s dog Olive Oyl set off in a covered wagon hitched to a three-mule team to cross the Oregon Trail. Buck, driven by what he calls “crazyass passion” and a romantic memory of a childhood trip he took with his father and siblings across Pennsylvania in a covered wagon, conceived of the trip almost on a whim. “Only a delusional jackass, or someone seriously off his medications, would pull off the road at the Hollenberg Ranch one fine summer afternoon and concoct such a preposterous scheme,” he writes.

But you can’t save an addictive dreamer from himself, and that jackass happens to be me. Already, powerful forces were drawing me west. I felt an irresistible urge to forsake my life back east for a rapturous journey across the plains.

Rinker is clearly a romantic and throughout the book he walks a fine line between romanticism and reality. In fact, this duality informs much of the book. Even as Rinker is drawn to a romantic vision of the trail, waxing poetic about life in the wagon and how he never wants the trip to end, he complicates that vision of the trail with historical fact and his own experience. Whether discussing the trail itself, the relationships between the pioneers and the native tribes, the history of mule breeding, or even the genesis of the word “pioneer,” nothing is as simple as it seems.

Helping to tip the scales more towards the reality end of the spectrum is Rinker’s brother Nick. Nick is a consummate tinkerer and free spirit, the opposite of Rinker in many ways. “I am bookish and neat,” Rinker writes, “with a fondness for antique furniture, good wine, and clean cars. If I am depressed or have writer’s block, I spend the afternoon logging in the woods or ironing my Brooks Brothers shirts. Nick buys a new Carhartt shirt at Reny’s Discount in Damariscotta and breaks it in by using it as an oil rag on the way home.”

Watching the relationship between the two brothers deepen as they learn to appreciate each other is one of the most enjoyable parts of the book. While Rinker has a tendency to brood and struggle with the differences between simple ideals and the complications of reality, Nick, however, has no such compunctions. “There’s no fuckin cure for any of us, Rinker,” Nick tells his brother. “Get into it dickhead. I’m fucked up, you’re fucked up, okay? Fucked up is normal.” And while Rinker both dreams up and plans out the trip, examining maps and historical records of the trail, Nick, with his encyclopedic knowledge of the workings of wagons and mules, quickly proves himself an ideal, if not essential, trail companion.

The brothers together face the many challenges inherent in traveling the trail and it doesn’t take long for them to figure out what every adventurer figures out eventually. “This is just a whole lot of work,” Nick puts it succinctly on the first afternoon. Hitching the mules, a dangerous and nerve-wracking undertaking on the best of days; staying awake in the driver’s seat so as not to fall and get crushed under the wagon wheels; finding clean water and places to camp; bathing, feeding, watering, and generally caring for the mules; figuring out the best route—all of this is hard work they must deal with on a daily basis. On top of that are stretches of challenging terrain, nasty weather, and bridges that spook the mules, among many other things.

However, it also doesn’t take long for them to learn another lesson that every adventurer also eventually learns: no one does any of this alone. The Buck brothers find that along the trail, hardly a day goes by when someone doesn’t offer help in some way. Ranchers show them the best places to camp and give them advice on the route they should take; trail historians pass along valuable information both about the historical trail and its current condition; kids come out to feed apples to the mules and play with Olive Oyl; people take them in, offering them meals and showers and all sorts of kindnesses. The acknowledgements section at the end reads like its own chapter and is well worth looking through, if for no other reason than to appreciate the generosity offered.

There’s something about pushing yourself to accomplish a feat most people would write off as insane that can make you feel alive in ways you never knew possible. Facing the insurmountable, making mistake after mistake after mistake, and loving every minute of it—this is adventure. “The wrong outcome, or no outcome at all, is often the only result of a journey,” Rinker writes, reflecting on what his journey meant in the end.

The impossible is doable as long as you have a great brother and good trail friends. Uncertainty is all. Crazyass passion is the staple of life and persistence its nourishing force. Without them, you cannot cross the trail.