One evening I stumbled across an item reporting that a cyclist had mapped a bikepacking route along the Pony Express Trail. The route was two thousand miles long, ran across seven states from Missouri to California, and as it followed the trail as closely as possible, was eighty-five percent off-road. I knew right then I had to ride it. What I didn’t know was why.

I used to ride ultra-distance cycling events, but that was more than a decade earlier, over paved roads on a lightweight, skinny-tired bike. I had crashed a couple of years earlier and had since only ridden a mountain bike on fun, short, low-speed, off-road trails. Bikepacking was the worst combination of both: long days riding everything from busy highway shoulders to sketchy trails through remote terrain; carrying with me everything I’d need to survive—camping gear, food, clothing, tools, extra water; and doing it all on a slow, heavy bike.

Plus, I had no bikepacking equipment. I owned a full-suspension mountain bike, which could not carry all the equipment and food I’d need. I owned no camping gear, and in fact had not camped in decades—my partner and our teenage son both refuse to camp on principle. Even if I started planning and training and buying equipment like a madman right then, I would still need a year to gather the gear, test it, and train. By then I’d be 62 years old, not the ideal age to start a five-week solo ride across some of the most remote areas of the American West.

And yet, there it was: someone had laid out a Pony Express bikepacking route and I knew I had to ride it or regret missing the opportunity the rest of my life. Even if it killed me.

By some turn of fate, not long after I had committed myself to bikepacking the Pony Express Trail most of us found ourselves locked down under shelter-in-place orders in an attempt to slow the spread of COVID-19. What the stay-at-home order took away from me in terms of training opportunities though, it gave back in the form of time to research the history of the trail.

As it turns out, there is very little primary documentation about the Pony Express. No one wrote a book-length treatment of the service until fifty years after it ended. By then very few company records still existed, and only a handful of former employees were still alive. As a result of this paucity of documentable proof, at every turn I would read an often-recited “fact” that turned out to be pure fiction. For example, nearly every popular work states that riding for the Pony Express was so dangerous, ads calling for riders specified, “Orphans preferred.” No such ad ever ran.

On the other hand, very few Pony Express narratives point out that the owners of the company were slaveholders who supported violent proslavery forces in Bleeding Kansas. This discrepancy is indicative of most Pony Express literature: chroniclers tend to amplify positive stories about the Pony Express and to downplay, explain away, or most often, just ignore the negative aspects. The overall effect of this overwhelmingly positive press is to elevate, almost to canonize the lone rider and the stout-hearted pony as paragons of American fortitude, the Pony Express as the epitome of the determination that won the west.

Once the few items of supportable facts are exhumed from under the tailings pile of embellishments, however, the Pony Express emerges as one of the least dynamic facets of its era. Reduced to its essence, all the Pony did was substitute riders and horses for electrons, because mostly the Pony just relayed short messages between the easternmost and westernmost telegraph stations. As the reach of the telegraph spread, the route of Pony Express shrunk, until the telegraph wires finally connected from coast to coast and the Pony Express winked out of existence, as if the switch that turned the telegraph on simultaneously turned the Pony Express off.

It came, it ran, it died an ignominious death.

But while the Pony Express may be among the least significant developments of its era, it is the most iconic. As such, it is an ideal perch, a central platform on which to stand and to take in at a glance the panoply of monumental events swirling around it, because one can’t really understand the Pony Express—what it stood for, what it accomplished, why it came about at all—without understanding the far more interesting historical milieu out of which it arose: The Mexican-American, Utah, and Paiute Wars; the California and Pike’s Peak gold rushes; the overland emigration of hundreds of thousands to Oregon and California; the exodus of tens of thousands of Mormons to Utah. Underlying these monumental events are the equally important political and societal currents of the era: the acquisition of Oregon, California, and New Mexico; the persecution of Mormons across the Midwest; the development of Trans-Mississippi freighting and stagecoaching; government and civilian relations with Native Americans; the role of US Mail in developing the west; the placement and deployment federal troops and forts along the Emigrant Trail; and finally, casting a shadow over every aspect of United States history in this period, the increasingly contentious fight over slavery along with the looming threats of state secession and civil war.