Alta Journal is pleased to present the third installment of a five-part original series by geologist and author Ruby McConnell tracing the creation of the Applegate Trail.

In the fall of 1843, hundreds of trail-weary U.S citizens arrived at the eastern edge of the Oregon territory. They were members of the first pioneer wagon train, the beginning of what would come to be a massive migration. They had been lured west by promises of easy prosperity and the rhetoric of manifest destiny. In truth, the migration was orchestrated by the federal government, which needed to “occupy Oregon” in order to claim its land and resources from competing colonial nations. In that first train were the brothers Applegate, whose arrival in Oregon was marred by the loss of two of their sons in a tragic river accident. It was an incident that foreshadowed much of their experience of the Oregon Country, where fortunes, reputations, and family were always at risk. Ruby McConnell brings the story of the Applegates and other tales of the American West to life through her extensive research of archival material and reporting in her forthcoming book, Wilderness and the American Spirit (Overcup Press, 2024).

alta serials, applegate trail
Alta

Four weeks after losing Edward and Warren, both just nine years old, to the river, the Applegates arrived at Fort Vancouver, near the confluence of the Willamette and Columbia Rivers. They had made it, but their hearts were broken. The brothers were determined that as soon as their families were settled, they would look for another, safer way for future travelers to get to the Oregon Country.

Having at last arrived there, the brothers looked south into the Willamette Valley and envisioned their future. In that future, they would have seen summer fields golden brown with wheat, orchards bursting with hazelnuts and apples, and acres and acres of pumpkin and corn in the fall. On what few rises exist across the wide, flat valley, they imagined houses, whitewashed and meticulously kept, rosebushes dotting the ends of each property, and weeping willows forming natural gazebos in every yard. Beyond the houses, the faintest outline of a town. But not yet.

The notion of establishing a new life of their own design out West, the tale spun for them by the government and missionaries like Marcus Whitman, was still enticing, even with the hardships behind them and the unknowns before them. This was especially true for Jesse, who stood apart from his brothers by education and ambition. A college graduate trained as a surveyor, he’d come to the Oregon Country with the goal of entering politics.

The immediate problem, though, was still survival. The group pushed south into the valley, taking up winter residence at the old abandoned Methodist Mission in the present-day state capital, Salem. From there, they could recuperate, replenish their food stores, reunite with their cattle, and search for homesteads, and Jesse could gain access to the burgeoning provisional government.

Methodist missionaries had constructed the small group of buildings in 1834 with the goal of converting Indigenous inhabitants to their faith. It hadn’t worked, and eventually the missionaries abandoned the endeavor and their buildings. Now the mission served as temporary shelter for whoever came upon it and as a gathering place for nearby homesteaders. The plain wooden buildings did little to keep out Oregon’s cold rains, but they would have to do.

At the mission, the brothers got to work. Charles, whose wife, Melinda, was already pregnant with another child, worked as a blacksmith that first winter. Jesse worked as surveyor general for the territory, and as his friend Robert Shortess had predicted in his letters enticing him to make the journey, he was easily elected to the legislative assembly. Lindsay had operated a gristmill in St. Louis and figured he’d do the same in Oregon, but he wasn’t opposed to going wherever the wind blew him. All three kept their eyes open for their ideal homestead.

Meanwhile, each year more and more new people poured into the Oregon territory, many recounting similar stories of dangerous conditions on the trail and death on the river. In one incident, an entire family drowned trying to navigate the same river run that had taken the Applegates’ children. The brothers continued to insist that there had to be a better passage.

The notion of establishing a new life of their own design out West was still enticing. The immediate problem, though, was still survival.

As the population grew, the provisional government worked toward statehood. Complicating the matter was the issue of boundaries. At the time, Oregon was still disputed territory, especially in the south where few had established homesteads. To hold the territory and define its borders, the United States would likely have to take up arms against either Spain or Great Britain. But there was no land access to the disputed borderlands and no way to transport goods or military men and munitions without traversing the cumbersome northern route or relying on ships. They needed a southern road.

The Applegates loved the idea. They saw the government’s plans for a southern road as an opportunity to find a safer route that would avoid the Columbia River. It seemed likely that such a route existed. Mountain men, hunters, and trappers had been using a network of Indigenous people’s foot trails for decades. Charting a southern road might be a matter merely of connecting the trails. Some of the trail network had even been mapped. Jesse seized on the idea and introduced legislation that would fund a road-hunting expedition.

In 1846, a company of just over a dozen men set out along those old trails with Jesse as the surveyor and Lindsay along with him as a scout. (They left Charles at home with the three families.) Jesse knew that his capacity as an elected official would put him under scrutiny. In those days, everything from government business to gossip was published in the papers. Before the company’s departure, the press had published high praise for the expedition, the brothers, and Jesse in particular. They even took to calling him the “first citizen of Oregon.”

His survey skills, everyone hoped, would be key to the group’s success. But Jesse knew that if they, like an earlier group who had attempted to find a route, failed, it would also be put on him. It was his name on the legislation.

The group did well at first, making the relatively easy climb out of the Willamette Valley and following the somewhat mapped trails into the Umpqua Mountains. But there, they began to doubt whether a true road, one suitable for large groups of soldiers and their equipment or for wagons and families, was possible. The canyons were narrow, and the ground was littered with loose rock, boulders, and fallen trees. It was hard going in good weather by strong men on foot. But they knew that the other side of the mountains was less rugged, that it opened onto the flatlands of the high desert and the weather was better. They hoped that a navigable route through the mountains existed. They just had to find it.

Remarkably, they did. A passable route did exist, mostly. Almost certainly with some improvements, which they were sure could be completed quickly. It wouldn’t be a pretty road, but it would be a serviceable one. Even with the route’s rough edges, the brothers were sure it would be safer than the northern river route.

By fall, the men reached the head of the California Trail in northern Nevada. There, the company broke up. One group was to prepare the trail for wagons; the other was to continue east to Fort Hall, Idaho, to promote the new route and serve as guides. But failure of communication, prior obligations, and lack of dedication got the better of them. Historical records regarding the subsequent events are incomplete and contradictory, but their effects are excruciatingly clear.

A few of the men, including, perhaps, the Applegates, broke from their groups early to return home. Somehow, portions of the new trail never got improved. That, combined with poor planning, worse weather, and a justified campaign of harassment by Indigenous people who were protecting their territory, would have fatal consequences.•

PART FOUR: THE END OF THE LINE »

Visit altaonline.com/serials to keep reading ‘That Damnable Applegate Road,’ and sign up here for email notifications when each new installment is available.

Headshot of Ruby McConnell

Ruby McConnell is a writer and geologist who writes about the intersection of the natural world and human experience. She is the author of the critically-acclaimed outdoor series A Woman’s Guide to the Wild and A Girl’s Guide to the Wild and its companion activity book for young adventurers, and Ground Truth: A Geological Survey of a Life, which was a finalist for the 2021 Oregon Book Awards. She lives and writes in the heart of Oregon country. You can almost always find her in the woods. She's on Twitter at @RubyGoneWild.