Meet the Man Who Spent His Summer Hiking More than 2,400 Miles of the Oregon Trail

For most people, the Oregon Trail exists in the past. Maybe it’s how their family first came to the west, or maybe it was part of their ancestors’ displacement. For some, it’s just a chapter from a history textbook; for others, it summons the computer game of the same name that almost always ended in an untimely death due to dysentery.

But not for Don Martin.

From April to July of this year, Martin was braving gusty winds, tornadoes, and stifling heat as he trekked 2,475 miles while pushing a makeshift covered wagon, dressed in period garb. His goal: to re-create the Oregon Trail experience as it was in the 1800s—and bring some recognition to a historic trail that he says has been mostly forgotten.

“I’m trying to regenerate some of that interest or some of that awareness of what the trail was, what people went through,” says Martin. “They [set] off literally into the unknown, with nothing more than a basic trail guide.”

The trip took Martin 95 days on foot, during which he walked along (mostly) roadways that almost 200 years ago were part of the original wagon route. (That’s a long time to be hoofing it, but back in the 1800s, the trip usually took four to five months.) In between sleeping in motels during stormy nights, Martin says he was happiest when he could simply lay out his bedroll and sleep under the stars with the coyotes, pronghorn, and owls.

“The real core of their experience was simply putting one foot in front of the other for more than 2,000 miles,” says Martin. “They rolled the dice in a way that is hard for us to even begin to understand.”

A Prineville resident and navy veteran, Martin acquired the nickname “Dundee” for the wide-brimmed hat that he had worn while trekking the Appalachian Trail. (He’d bought the hat while on reserve duty in Australia, which contributed to the Aussie-film-character-inspired name).

Before hiking the entire route, he’d previously done a 600-mile segment. “There’s a branch of the Oregon Trail that cuts off right by my house, so I started with that last year. It went up to The Dalles, and then down the Gorge to Portland,” Martin says. But that was just the warm-up. His full-length hike began in Independence, Missouri, the original jumping off-point for the Oregon Trail, and went all the way to Oregon City.

“There was a very persistent set of extremely strong storms during the first few days [on the trail]. I tried to get ahead of them. Eventually it covered the entire green plains so I just had to deal with it and find shelter indoors when I could,” he says. “And then the weather was pretty benign for a while until I got about halfway through Idaho, when there was a stretch of 100-degree days. And then again when I crossed into Oregon. It’s hard to step off into the unknown. There are hazards. It’s desert. And you can die out there if you don’t have your ducks in a row.”

Martin’s covered wagon wasn’t just for show. Just like the pioneers, he used it to carry necessities like food and water, with dried meat and fruit that would have seemed familiar to 1840 and 1850s trail users. And just like many of us like to name our cars, Martin named his wagon Ollie after the phrase “olly, olly, oxen free” from children’s games. (He even affixed a bumper sticker of sorts, a sign reading: “Oregon City or Bust.”)

His trip wasn’t “oxen free” for long. Some friends gave him a cape-wearing stuffed steer the named “Last Ox” after a graphic from the Oregon Trail game that he’d attached to the wagon cover, which read “Last Ox Wandered Off.”

 “What’s a wagon without an ox?” he asks. “Eventually the consensus was, I couldn’t be sent out alone. I had to have a companion.”

Using an Oregon Trail guide published by the National Park Service that he describes as “a collection of dots on the map,” Martin plugged the route in a GPS.

“I had maps from a couple people who did it, one by bicycle and one hiking, and so I had some idea of the roads that went through. The reality today is the Oregon Trail is not a trail in the sense that the Appalachian Trail is, where there’s a footpath to hike along. So you’re going to be walking on roads for nearly the whole trip,” he says.

He quickly found out that some parts of the trail can’t be accessed since they’re on private property. “In Lawrence, Kansas, I talked to a couple of people who are landowners, and the National Park line ran right through their property. Neither had any idea that they lived near the Oregon Trail,” says Martin. “One of them had a beautifully preserved swale running right through his backyard.” (Swale is another term for the rut or depressions left in the ground from wagon wheels—in Oregon, you can see nearly a mile of well-preserved wagon ruts at Echo Meadows Park, off I-84 to the west of Pendleton.)

Actually walking the entire wagon route is not for everyone. “Unfortunately, out of the over 2,000 miles, there’s only about 300 miles of actual trail left,” says Robin Baker, a volunteer with the Northwest chapter of the Oregon-California Trails Association, a nonprofit headquartered in Independence, Missouri, that works to preserve sections of the trail.

Baker leads group hikes along local trail sections such as the Barlow Road, which skirts Mount Hood from The Dalles to the Sandy River. “It just shows that somebody at least nowadays can do that,” says Baker of Martin’s trek from Missouri to Oregon. “You can also bicycle it,” he suggests. “I think that would make the boring parts—walking along the freeways—go a lot quicker.”

While the Oregon Trail is not nearly as popular to hike as say, the Pacific Crest Trail, Martin is hoping to change that. To date, he knows of just a handful of people, fewer than 10, he says, who’ve walked the entire route from end to end.

“What made this trip hard is because basically there are no facilities, no accommodation, no information for people who might want to walk it,” he says. Now that he’s finished his trek, Martin is planning to put together an Oregon Trail hiking guide using tips he’s picked up along the way, GPS information, and photos. “There are people who hike the Pacific Crest Trail every year and it’s a thing. I would like to see the Oregon Trail become a thing. It was a remarkable thing for people to do,” he says of those who traversed the original trail. “And it’s not that difficult to reconnect with their experience.”