Alta Journal is pleased to present the final installment of a five-part original series by geologist and author Ruby McConnell tracing the creation of the Applegate Trail.
All across Oregon are signs, markers, and information kiosks commemorating the Applegate Trail, though few residents recognize the name and fewer still can trace its path across the map. In 2016, Ruby McConnell set out to find this mysterious trail, and in doing so, she uncovered the lost story of the brothers Applegate—Charles, Jesse, and Lindsay—who failed to create a safer road to the Oregon Territory yet charted a route that became one of the most important transportation and commercial arteries of the American West. 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).
“Sometimes history is like old gossip. Just be aware of that,” Susan Applegate told me over a cup of coffee in 2019. Applegate is the great-great-granddaughter of Charles Applegate and the keeper, along with her cousin Shannon Applegate, of the family’s ancestral home, as well as its lore. I leaned in, trying to appear casual. I had, after all, been tracking the Applegates and their elusive emigrant trail for the past three years and had yet to separate fact from fiction.
What’s important to know, Applegate was eager to tell me, is that the Applegates, Jesse especially, were good, even brilliant, pathfinders, regardless of anything else I might read or hear. Her rush to assure me of their competence and, later in the conversation, their moral compass was an answer to the question I’d been asking for three years: Why hasn’t anyone heard of the Applegates or their emigrant road?
The brothers’ story is uniquely compelling. It has all the tragedy, grit, and toil of a classic western but with none of the Hollywood tropes. The Applegates never lucked out on oil or gold; they never rode off into the sunset. Charting the route was an achievement that should have secured their place in history alongside other famous pioneers and pathfinders. Their trail became a mainstay of regional transport, moving people, gold, and timber across once-difficult terrain. Instead, they faded from history under a cloud of controversy, paying the price for their adventurous spirit in the loss of loved ones.
Today, the approximate path of the Applegate Trail has been converted into portions of Highway 99 and the I-5 corridor, connecting Salem and Ashland, and Highway 140, which runs east over the mountains to eventually join what is now Interstate 80 in Nevada.
My interest in the Applegates didn’t start with the family, their tragedies or legacy. For me, it started with the road. The Applegate name is scattered across Oregon: Applegate Valley, Applegate Lake, the Applegate River. But I, like most people, had never really stopped to wonder why these particular places were named after this particular family.
And then, one day, I did.
“Turn left,” I remember saying to my husband. “That sign said Applegate Trail Interpretive Center. I want to see what it is.” What it was was a faded interpretive sign at a dingy parking lot of a seemingly unused county park outside Veneta. The sign provided little information. A few weeks later, we followed a similar sign to a kiosk in a city park in Corvallis. Twice we chased signs without ever being able to find the associated “interpretive center.” Three years and dozens of similar detours later, I found myself having that cup of coffee with Susan Applegate.
By that time, I had begun to piece together the story of the Applegates and their importance to the early development and political landscape of Oregon. But it turned out that finding information about the lives of these “road hunters” was as challenging as following their trail.
A lot of the Applegate story is forgotten, embellished, or disputed, which is why portions of the trail are still left unnamed, renamed, or unmarked on maps. There are books about the Applegate Trail, though many are out of print. One called A Day with the Cow Column in 1843 (1868) was written decades after the events described, most of which occurred when the author was just a child.
Even modern accounts, such as Shannon Applegate’s Skookum: An Oregon Pioneer Family’s History and Lore (1988), which relies heavily on diaries, letters, and other original source material, often veer into speculation and, in places, downright fantasy. Further obscuring the story is the problem of naming. A Day with the Cow Column was written by Jesse Applegate Applegate, Lindsay’s son. But most editions of the book simply list the author as Jesse A. Applegate, and the resulting confusion can be traced through reference materials as researchers conflate the two Jesses, resulting in a tangling of their histories.
And it goes on like this, with many of the Applegate brothers’ nearly 40 children named for significant figures or influences in their parents’ lives: Oliver Cromwell Applegate, Robert Shortess Applegate, and Peter Skeen Ogden Applegate, among them.
In 2020, at the height of the COVID-19 pandemic, I decided to try to untangle the Applegate story, starting with the road. I wanted to see for myself the route that Jesse and Lindsay had charted. I set out to find as much of the Oregon portion of the trail as I could.
What remains of the original path, it turns out, is little more than a few traces of wagon ruts covered in poison oak and some scattered plaques affixed to railroad ties and mounted on posts. Searching for these markers was like an Easter egg hunt. They stand, barely visible, in fields along the freeway, in rural fire station parking lots, next to country chapels, at roadside pullouts, or on tiny parcels of county and municipal land.
That the trail is marked at all is a marvel, since it passes through a vast and harsh landscape with few amenities to offer travelers even today. Winter storms, much like those that caused so much trouble for emigrants in 1846, can still strand motorists today. The majority of the trail’s markers are not on major roads. These markers are the result of the efforts of a dedicated team of people who diligently pored over diaries and first-person accounts to find the trail’s remnants. It is possible, though not easy, with the help of other guides and several maps, to follow the markers for most of the trail’s 500-mile length.
Easier to find was the Charles Applegate house. It stood quiet and closed to public entry but retained its essential character. Whitewashed, with low ceilings and broad balconies, it still overlooks the Yoncalla Valley. If one observes the house from the end of the long lane that leads to it, one might wonder whether any time has passed at all.
But time has passed. Yoncalla never became the great western city the Applegate brothers might have envisioned. It is a nothing town in the middle of nowhere, a failed place at the base of a defunct mine that is now a Superfund site. The original Applegate Trail, which primarily follows the old Highway 99, lies a quarter mile to the west of the house, which is paralleled a short way to the east by a still-active rail line. Beyond the rails, cars and trucks roar past on the interstate highway. A row of cell towers overlooks them all from atop the foothills of the Cascades. These are the markers of progress, signs of the time made possible by the charting of that southern route.
Following the Applegates’ trail, I found their legacy someplace at the intersection of history and gossip. The Applegates were good road hunters and, like all of us, imperfect people. More than anything, their story illuminates the ways in which we collectively bend history to fit our notions of heroes and villains. This is especially true in the old American West, where circumstance and the struggle for survival often placed the best and worst of humanity alongside one another.
The Applegates’ experience of emigration west and their time in Oregon proved as tortuous as the trail that bears their name. In their story, no one struck it rich, and reputations were lost, not made. And yet, it’s still a great American story, one that left a mark on the American West that remains into the 21st century.•
Visit altaonline.com/serials to read every installment of ‘That Damnable Applegate Road,’ and sign up here for email notifications for future Serials.
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.
